3-Amino-4-methoxybenzanilide → 3-[3-(3,4-Dimethoxyphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide

HRID 1859692Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.972 g, 4.0 mmol), 3,4-dimethoxyphenyl isothiocyanate (0.787 g, 4.0 mmol), and ethyl acetate (25 mL) was heated briefly to 50° C. and then allowed to stand overnight at room temperature. The reaction mixture was diluted with ethyl acetate (˜100 mL), heated to 80° C. briefly, then allowed to stand 5 days at room temperature. The precipitate was filtered off to afford the product (0.552 g); m.p. 170-171° C.

Workup

temperatureheated to 80° C. briefly
waitto stand 5 days at room temperature
filtrationThe precipitate was filtered off

Sources & evidence

ORD record: ord-c67a814e562e4258b488ef27aac87fc2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

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