N-[4-(Benzyloxy)phenyl]thiourea → Methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide

HRID 412972Notes

Reaction equation

HRID 412972 reaction equation
CSC1SC(C(OC)=O)=CC=1C1[N:13]=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[S:15]C=1.[Br:32][CH2:33][C:34]([C:36]1[CH:37]=[C:38]([C:42]([O:44][CH3:45])=[S:43])[S:39][C:40]=1[CH3:41])=O.C(OC1C=CC(NC(N)=S)=CC=1)C1C=CC=CC=1>>[BrH:32].[C:26]1([CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([NH:17][C:14]3[S:15][CH:33]=[C:34]([C:36]4[CH:37]=[C:38]([C:42]([O:44][CH3:45])=[S:43])[S:39][C:40]=4[CH3:41])[N:13]=3)=[CH:19][CH:20]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 2060579N-[4-(Benzyloxy)phenyl]thioureaHCID 18537080Methyl 5-methylthio-4-(2-{[4-(phenylmethoxy)phenyl]amino}(1,3-thiazol-4-yl))thiophene-2-carboxylateHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583836Methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromideYield 76%

Procedure

Methyl 5-methylthio-4-(2-{[4-(phenylmethoxy)phenyl]amino}(1,3-thiazol-4-yl))thiophene-2-carboxylate: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (336.3 mg, 1.08 mmol) was allowed to react with 4-benzyloxyphenyl thiourea (279 mg) as described in Example 154, step (a) to give 450 mg (76% yield) of methyl 4-(2-{[4-phenylmethoxyphenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide. Mass Spectrum (ESI) m/z calcd. for C23H20N2O3S3, 468.61 (M+H), found 469.2.

Sources & evidence

ORD record
ord-69e06b7e908f45e696d5c9a156dce469
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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