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

HRID 2186619Notes

Reaction equation

HRID 2186619 reaction equation
Br.[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[S:17][CH:18]=[C:19]([C:21]3[C:25](=[CH2:26])[S:24][CH:23]([C:27]([O:29][CH3:30])=[S:28])[CH:22]=3)[N:20]=2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:31]CC(C1C=C(C(OC)=S)SC=1C)=O.O(C1C=CC(NC(N)=S)=CC=1)C1C=CC=CC=1>>[BrH:31].[O:2]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:22]=[C:23]([C:27]([O:29][CH3:30])=[S:28])[S:24][C:25]=3[CH3:26])[N:20]=2)=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 27603494-PhenoxyphenylthioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylateHCID 131723300Methyl 4-(2-{[4-phenoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methlylthiothiophene-2-carboxylate hydrobromide

Product 1

HCID 86758183Methyl 4-(2-{[4-(phenoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromideYield 88%

Procedure

Methyl 4-(2-{[4-phenoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methlylthiothiophene-2-carboxylate hydrobromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (200 mg, 0.64 mmol) was allowed to react with 4-phenoxyphenylthiourea (158 mg) as described in Example 154, step (a) to give 300 mg (88% yield) of methyl 4-(2-{[4-(phenoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide. Mass Spectrum (ESI) m/z calcd. for C22H18N2O3S3, 454.6 (M+H), found 455.2.

Sources & evidence

ORD record
ord-a997534ccec04ea99e34c0f5fa213b9e
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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