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

HRID 1840338ノート

反応式

HRID 1840338 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-25abe7e906a74eb59399af693a1ab546
出典データセット
uspto-grants-2004_01
特許番号
US06680317B2

反応ノート

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