Hydrogen Sulfide → o-Dimethoxymethylthiobenzamide
Reaction equation
C(C1C=CC=CC=1C1[S:10]C=C(C2C=CC=CC=2)N=1)=O.[CH3:20][O:21][CH:22]([O:31][CH3:32])[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26].S>>[CH3:20][O:21][CH:22]([O:31][CH3:32])[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]([NH2:26])=[S:10]Participants
Procedure
A solution of 2.65 g of 2-(o-formylphenyl)-4-phenylthiazole [M.P. 99°-100°; obtainable by reacting o-dimethoxymethylbenzonitrile with H2S to give o-dimethoxymethylthiobenzamide (M.P. 100°-102°), reacting the latter with α-bromoacetophenone to give o-dimethoxymethylthiobenzoic acid imide S-phenacyl ester (oil), and cyclizing the latter to give 2-(o-dimethoxymethylphenyl)-4-phenylthiazole by boiling with methanol and subsequent hydrolysis with aqueous hydrochloric acid], 1.06 ml of 33% aqueous ammonia, 2.32 g of methyl acetoacetate and 120 ml of methanol is boiled for 18 hours and evaporated. Treating the residue with ether gives 2,6-dimethyl-3,5-dimethoxycarbonyl-4-o-(4-phenyl-2-thiazolyl)-phenyl-1,4-dihydropyridine, M.P. 145°-148° (decomposition).
Sources & evidence
- ORD record
- ord-4b70fc487a3443fe95164de88ca8f8c3
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766213
Reaction notes
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