Benzoyl isothiocyanate → 1-Benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea

HRID 51862

반응식

HRID 51862 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[NH2:26].[C:27]([N:35]=[C:36]=[S:37])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O.C(OCC)(=O)C>[C:27]([NH:35][C:36]([NH:26][C:4]1[CH:5]=[C:6]([N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[S:37])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 227369664-methoxy-N1,N1-bis-(4-methyl-benzyl)-benzene-1,3-diamine

생성물 1

HCID 220157381-Benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea수율 80%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 400 mg (1.15 mmol) 4-methoxy-N1,N1-bis-(4-methyl-benzyl)-benzene-1,3-diamine in 8 ml acetone was added dropwise a solution of 0.18 ml (1.34 mmol) benzoyl isothiocyanate in 4 ml acetone and stirring continued for 30 minutes at room temperature. The mixture was then diluted with ethyl acetate and washed with water and then with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/9 ethyl acetate/hexane) afforded 320 mg (80%) 1-benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea as a yellow oil. ES-MS m/e (%): 510 (M+H+, 100).

후처리

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-94a7c999aaeb4fa3aa55984fa4b9e628
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

연결된 노트

불러오는 중…