Urea, 1-(4-chloro-o-tolyl)-2-thio- → HCID 86583831, compound

HRID 2298646Notes

Reaction equation

HRID 2298646 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.[CH3:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24]([NH2:26])=[S:25]>>[BrH:1].[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([NH:23][C:24]2[S:25][CH:2]=[C:3]([C:5]3[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=3[CH3:10])[N:26]=2)=[C:16]([CH3:15])[CH:21]=1

Participants

3

Reactant 2

HCID 2757702Urea, 1-(4-chloro-o-tolyl)-2-thio-HCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583831HCID 86583831, compoundYield 81.7%

Procedure

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (50 mg, 0.16 mmol) was allowed to react with 2-methyl-4-chlorophenyl thiourea (32.1 mg) as described in Example 154, step (a), to give 62.2 mg (79% yield) of methyl 4-{2-[(4-chloro-2-methylphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-6, 300 MHz) δ2.28, 2.29 (s, 3H rotomer), 2.62, 2.66 (s, 3H rotomer), 3.82 (s, 3H), 7.21-7.29 (m, 3H), 8.04, 8.11 (s, 1H rotomer), 8.17 (d, 1H, J=8.8 Hz), 8.30 (d, 1H, J=8.4 Hz), 9.44 (s, 1H), 9.59 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C17H15ClN2O2S3, 410.96 (M+H), found 411.1.

Sources & evidence

ORD record
ord-573e161f43a148d8a31701d590206b0f
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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