참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | Ethyl (methylthio)acetate | HCID 78199 | — |
| 반응물 | Tert-Butyl hypochlorite | HCID 521297 | — |
| 반응물 | 3-(4-Amino-benzyl)-5-(4-chloro-phenyl)-3,6-dihydro-[1,3,4]thiadiazin-2-one | HCID 66636570 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | HCID 66636295 | HCID 66636295 | — |
반응 단계
To a solution of the compound obtained in Step C (38.27 mmoles), in a mixture of CH3CN (115 ml) and THF (115 ml) at −60° C., ethyl(methylsulphanyl)acetate (45.92 mmoles) is added dropwise under a nitrogen atmosphere. tBuOCl (45.92 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 1 hour at −60° C., triethylamine (51.66 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature. 240 ml of DCM and then aqueous 3M HCl solution (340 ml) are added. After stirring for 12 hours at ambient temperature, the reaction mixture is made alkaline (pH 10-11) using 20% aqueous sodium hydroxide solution. After extraction with DCM, the organic phase is washed with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is triturated in ethyl ether, filtered and dried in vacuo to yield the title product which is used directly in the next Step.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08541412B2 |
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| 출처 데이터셋 | uspto-grants-2013_09 |
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| ORD ID | ord-721b27c7426a4fe0a4a241c1f831b5ac |
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| 출처 메모 | uspto-grants-2013_09 |
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