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

HRID 2298660Notes

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.[O:15]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH2:31])=[S:30])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[BrH:1].[O:15]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]2[S:30][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:31]=2)=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Reactant 2

HCID 27603494-Phenoxyphenylthiourea

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

Product 1

HCID 86758183Methyl 4-(2-{[4-(phenoxy)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromideYield 90.2%

Procedure

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-c8bd5b0fd00b41e9883670c8443abd5d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492403B1

Reaction notes

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