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

HRID 51862

Reaction equation

HRID 51862 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-94a7c999aaeb4fa3aa55984fa4b9e628
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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