Imidazole → N-[4-Chloro2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)thiourea

HRID 1840338노트

반응식

HRID 1840338 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[S:10])=[C:4]([OH:20])[C:3]=1[S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].N1C=CN=C1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[S:10])=[C:4]([O:20][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:3]=1[S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10297913N-[4-Chloro-2-hydroxy-3[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2,3-dichlorophenyl)thiourea

생성물 1

HCID 23447765N-[4-Chloro2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)thiourea수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-[4-chloro-2-hydroxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3dichlorophenyl)thiourea (440 mg, 1.07 mmol) in THF (20 mL), tert-butyldimethylsilyl chloride (730 mg, 4.85 mmol) and imidazole (132 mg, 1.94 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours. Then it was partitioned between ethyl acetate and water. The combined organic phase was dried and concentrated. Chromatography of the residue on silica gel (30% Ethyl acetate/Hexane) gave desired product (270 mg, 50%). EI-MS m/z 570 (M+).

후처리

  1. customThen it was partitioned between ethyl acetate and water
  2. customThe combined organic phase was dried
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-25abe7e906a74eb59399af693a1ab546
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680317B2

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