N-(2,3-Dichlorophenyl)thiourea → HCID 86583840, compound

HRID 2298655Notes

Reaction equation

HRID 2298655 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.[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:23][C:24]([NH2:26])=[S:25]>>[BrH:1].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][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 2758213N-(2,3-Dichlorophenyl)thioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583840HCID 86583840, compoundYield 64.2%

Procedure

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (60 mg, 0.19 mmol) was allowed to react with 2,3-dichlorophenylthiourea (42 mg) as described in Example 154, step (a) to give 60.5 mg (62% yield) methyl 4-{2-[(2,3-dichlorophenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.66 (s, 3H), 3.82 (s, 3H), 7.27 (dd, 1H, J=1.5, 6.5 Hz), 7.36 (d, 1H, J=8.2 Hz), 7.43 (s, 1H), 8.14 (s, 1H), 8.62 (dd, 1H, J=1.5, 8.4 Hz), 9.95 (bs, 1H); Mass Spectrum (ESI) m/z calcd. for C16H12Cl2N2O2S3, 431.38 (M+H), found 431.1, 433.0.

Sources & evidence

ORD record
ord-fc3c18312e204caf90904cda4c619d63
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

Loading…