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| | 5-Chloroisatoic anhydride Basic information |
| Product Name: | 5-Chloroisatoic anhydride | | Synonyms: | TIMTEC-BB SBB003570;AKOS BBS-00002892;5-CHLOROISATOIC ANHYDRIDE;5-CHLOROISATONIC ANHYDRIDE;6-CHLORO-1,2-DIHYDRO-4 H-3,1-BENZOXAZINE-2,4-DIONE;6-chloro-4h-3,1-benzoxazine-2,4(1h)-dione;5-Chloroisotoic anhydride;6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione | | CAS: | 4743-17-3 | | MF: | C8H4ClNO3 | | MW: | 197.58 | | EINECS: | 225-255-7 | | Product Categories: | Benzoxazines;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts | | Mol File: | 4743-17-3.mol |  |
| | 5-Chloroisatoic anhydride Chemical Properties |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 2934999090 |
| | 5-Chloroisatoic anhydride Usage And Synthesis |
| Chemical Properties | White powder | | Uses | 5-Chloroisatoic Anhydride was used as a reagent in the synthesis of 2-acetamidobenzamides bearing the 2-phenoxy functionality which display antiproliferative activity against certain tumor cell lines. Also used in the preparation of inhibitors of delta-5 desaturase. | | Preparation | 5-Chloroisatoic anhydride is prepared from 5-chloro indole (9c) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature.
1 H NMR (DMSO-d6): δ 11.85 (s, br., 1H), 7.96 (dd, J = 0.8, 8.7 Hz, 1H), 7.87 (dd, J = 2.3, 8.7 Hz, 1H), 7.09 (dd, J = 8.8, 0.8 Hz, 1H).
| | Synthesis | Step 1 Synthesis of 6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione: 2-Amino-5-chlorobenzoic acid (17 g, 0.1 mol) and 1,2-dichloroethane (200 mL) were added to a 500 mL three-necked round-bottom flask. A solution of triphosgene (21 g, 0.21 mol) in 1,2-dichloroethane (100 mL) was slowly added dropwise to the above solution at 80 °C. After the dropwise addition was completed, the reaction mixture was continued to be heated and stirred at 80°C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature in an ice water bath. The precipitated white solid precipitate was collected by filtration and washed with an appropriate solvent and dried to afford 6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (19 g, 97% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 11.85 (br, 1H), 7.88 (d, J = 2.4 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.15 (d, J = 8.7 Hz, 1H). | | References | [1] Patent: US2010/120741, 2010, A1. Location in patent: Page/Page column 78
[2] Patent: WO2011/112731, 2011, A2. Location in patent: Page/Page column 174
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6434 - 6456
[4] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 444 - 454
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299 |
| | 5-Chloroisatoic anhydride Preparation Products And Raw materials |
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