2-bromo-4-methylphenylthiourea → Methyl 4-{2-[(2-bromo-4-methylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide

HRID 1058473Notes

Reaction equation

HRID 1058473 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.[Br:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24]([NH2:26])=[S:25]>>[BrH:1].[Br:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24]1[S:25][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=2[CH3:10])[N:26]=1

Participants

3

Reactant 2

HCID 40115382-bromo-4-methylphenylthioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758682Methyl 4-{2-[(2-bromo-4-methylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromideYield 62.7%

Procedure

Methyl 4-{2-[(2-bromo-4-methylphenyl)amino](1,3-thiazol-4-yl)}-5-methylhiothiophene-2-carboxylate hydrobromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (60 mg, 0.19 mmol) was allowed to react with 2-bromo-4-methylphenyl thiourea (47 mg) as described in Example 154, step (a) to give 62 mg (61% yield) of methyl 4-{2-[(2-bromo-4-methylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.28 (s, 3H), 3.82 (s, 3H), 7.19-7.23 (m, 1H), 7.27 (s, 1H), 7.48 (m, 1H), 8.14, 8.17 (s, 1H rotomer), 9.52, 9.72 (bs, 1H rotomer); Mass Spectrum (ESI) m/z calcd. for C17H15BrN2O2S3, 455.42 (M+H), found 455.0, 457.0.

Sources & evidence

ORD record
ord-f46b9aee479442938d11eb4dc47f72f5
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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