(4-(Benzyloxy)phenyl)thiourea → Methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide

HRID 2298651Notes

Reaction equation

HRID 2298651 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=O.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[S:31])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[BrH:1].[C:16]1([CH2:15][O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]3[S:31][CH:2]=[C:3]([C:5]4[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=4[CH3:10])[N:32]=3)=[CH:25][CH:24]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 2060579(4-(Benzyloxy)phenyl)thioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583836Methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromideYield 78.1%

Procedure

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (336.3 mg, 1.08 mmol) was allowed to react with 4-benzyloxyphenyl thiourea (279 mg) as described in Example 154, step (a) to give 450 mg (76% yield) of methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide. Mass Spectrum (ESI) m/z calcd. for C23H20N2O3S3, 468.61 (M+H), found 469.2.

Sources & evidence

ORD record
ord-06328f11ae884c41af87332ae7fca935
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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