참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Benzyl Bromide | HCID 7498 | — |
| 반응물 | Diethylthiocarbamoyl chloride | HCID 66607 | — |
| 반응물 | Cesium | HCID 5354618 | — |
| 반응물 | 4-Isopropyl-6-hydroxysaccharin | HCID 10037346 | — |
| 반응물 | 2-Benzyl-4-isopropyl-6-hydroxysaccharin | HCID 70044650 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 2-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin | HCID 86746562 | — |
반응 단계
Selective N-benzylation of the cesium salt of 4-isopropyl-6-hydroxysaccharin (Preparation 19) with benzyl bromide and reaction of the 2-benzyl-4-isopropyl-6-hydroxysaccharin with N,N-diethylthiocarbamyl chloride in DMF using the procedure described above in Preparation 12 affords 2-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin which, on heating, rearranges to 2-benzyl-4-isopropyl-6-(N,N-diethylcarbamyl-thio)saccharin. The latter, on hydrolysis with alkali, affords 2-benzyl-4-isopropyl-6-mercaptosaccharin which on reaction with methyl iodide, and transfer hydrogenolysis affords 4-isopropyl-6-methylthiosaccharin. Oxidation of the latter with one or two molar equivalents of 3-chloroperbenzoic acid affords 4-isopropyl-6-methyl-sulfinylsaccharin and 4-isopropyl-6-methylsulfonylsaccharin.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US05783589 |
|---|
| 출처 데이터셋 | uspto-grants-1998_07 |
|---|
| ORD ID | ord-b88a8425df884e628a17ce55bbde03ef |
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| 출처 메모 | uspto-grants-1998_07 |
|---|
