Benzyl Bromide → 2-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin

HRID 864747노트

반응식

HRID 864747 반응식
[Cs].C(C1C=C(O)C=C2C=1C(=O)NS2(=O)=O)(C)C.C(Br)C1C=CC=CC=1.[CH2:26]([N:33]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][C:39]([OH:48])=[CH:40][C:41]=2[CH:45]([CH3:47])[CH3:46])[S:34]1(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:49]([N:51]([CH2:55][CH3:56])[C:52](Cl)=[S:53])[CH3:50]>CN(C=O)C>[CH2:26]([N:33]1[C:43](=[O:44])[C:42]2[C:37](=[CH:38][C:39]([O:48][C:52](=[S:53])[N:51]([CH2:55][CH3:56])[CH2:49][CH3:50])=[CH:40][C:41]=2[CH:45]([CH3:46])[CH3:47])[S:34]1(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

7

반응물 5

HCID 7498Benzyl BromideHCID 66607Diethylthiocarbamoyl chlorideHCID 5354618CesiumHCID 100373464-Isopropyl-6-hydroxysaccharinHCID 700446502-Benzyl-4-isopropyl-6-hydroxysaccharin

생성물 1

HCID 867465622-benzyl-4-isopropyl-6-(N,N-diethylthiocarbamyloxy)saccharin

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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-methulsulfonyl-saccharin.

후처리

  1. customdescribed above in Preparation 12

출처 및 근거

ORD 기록
ord-0efe7b337a8d4b5586f61a2696e231d6
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563163

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