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

HRID 51840

Reaction equation

HRID 51840 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])=[CH:5][C:4]=1[NH2:15].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[C:16]([NH:24][C:25]([NH:15][C:4]1[CH:5]=[C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 227369974-methoxy-N1-(2-methoxy-ethyl)-N1-methyl-benzene-1,3-diamine

Product 1

HCID 220157361-Benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thioureaYield 61.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 1.89 g (8.99 mmol) 4-methoxy-N1-(2-methoxy-ethyl)-N1-methyl-benzene-1,3-diamine in 60 ml acetone was added dropwise a solution of 1.38 ml (10.3 mmol) benzoyl isothiocyanate in 30 ml acetone and stirring continued at room temperature for 30 minutes. The mixture was then concentrated in vacuo. Trituration in ether afforded 2.05 g (61%) 1-benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea as a yellow solid. ES-MS m/e ((Y)): 374 (M+H+, 100).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-0697fc9ae5cc4f7d92b2d26b6b40a87e
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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