| Identification | More | [Name]
3-Chloro-4-morpholino-1,2,5-thiadiazole | [CAS]
30165-96-9 | [Synonyms]
3-CHLORO-4-MORPHOLIN-4-YL-1,2,5-THIADIAZOLE
3-CHLORO-4-MORPHOLINE-1,2,5-THIADIAZOLE
3-CHLORO-4-MORPHOLINO-1,2,5-THIADIAZOLE
3-Chloro-4-N-morpholine-1,2,5-thiadiazole
3-MORPHOLINO-4-CHLORO-1,2,5-THIADIAZOLE
4-(4-CHLORO-1,2,5-THIADIAZOL-3-YL)MORPHOLINE
4-CHLORO-3-MORPHOLINO-1,2,5-THIADIAZOLE
4-CHLORO-5-MORPHOLINO-2,1,3-THIADIAZOLE
AKOS B020558
AKOS BB-9733
ART-CHEM-BB B020558
TIMTEC-BB SBB000450
3-Morpholine-4-chloro-1,2,5-thiadiazole
3-Morpholine-4-chloro-1,2,5-th
3-Mor-4-chloro-1,2,5-thiadiazole
4-(4-Chloro-1,2,5-thiadiazol-3-yl)morpholine 97%
3-MORPHOLINE-4-CHLORO-1,2,5-THIADIAZOLE 99+%
3-morpholine-4-chloro-1,2,5-thiazole | [EINECS(EC#)]
250-077-1 | [Molecular Formula]
C6H8ClN3OS | [MDL Number]
MFCD00274160 | [Molecular Weight]
205.67 | [MOL File]
30165-96-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
44-47 °C (lit.) | [Boiling point ]
307.8±42.0 °C(Predicted) | [density ]
1.462±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-0.18±0.10(Predicted) | [color ]
White to Off-White | [InChI]
1S/C6H8ClN3OS/c7-5-6(9-12-8-5)10-1-3-11-4-2-10/h1-4H2 | [InChIKey]
LAUCCQWGVCJGFT-UHFFFAOYSA-N | [SMILES]
Clc1nsnc1N2CCOCC2 | [CAS DataBase Reference]
30165-96-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
2934990002 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
Brown Solid | [Uses]
3-Chloro-4-morpholino-1,2,5-thiadiazole (Timolol EP Impurity F; Timolol BP Impurity F; Timolol USP Related Compound F) is an intermediate for the synthesis of Timolol. | [Uses]
An intermediate for the synthesis of Timolol | [Synthesis]
The general procedure for the synthesis of 3-chloro-4-morpholino-1,2,5-thiadiazole from morpholine and 3,4-dichloro-1,2,5-thiadiazole was as follows: morpholine (6.75 g, 77.4 mmol) was added to a 100-mL three-necked flask assembled with a reflux condenser tube. The flask was heated to 110 °C and 3,4-dichloro-1,2,5-thiadiazole (3.0 g, 19.3 mmol) was slowly added dropwise over 20 min. After the dropwise addition was completed, the reaction temperature was kept at 110°C with stirring for 2 hours. After completion of the reaction, the reaction mixture was cooled to 0°C in an ice bath. Water (30 mL) was added and the mixture was acidified with concentrated hydrochloric acid. The mixture was stirred at 0 °C until a precipitate precipitated. The solid product was collected by filtration, washed with water and dried. The resulting orange solid was recrystallized by methanol and dried under high vacuum to give 3.5 g (87.9% yield) of 4-(4-chloro-1,2,5-thiadiazol-3-yl)morpholine. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.45-3.55 (m, 2H), 3.80-3.90 (m, 2H). Mass spectral analysis showed (M + H)+ = 206.1. | [References]
[1] Synthesis, 2004, # 10, p. 1625 - 1628
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 14, p. 5281 - 5289
[3] ChemMedChem, 2015, vol. 10, # 2, p. 253 - 265
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 26, p. 6641 - 6644
[5] Angew. Chem., 2014, p. 6759 - 6762,4 |
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