Water → 5-(4-Formylphenoxy)thiophene-2-carboxamide

Reaction equation

[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:18].[K+].[K+].O>CS(C)=O>[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[S:12][C:11]([C:13]([NH2:14])=[O:18])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

Procedure

Dissolve 5-(4-formylphenoxy)thiophene-2-carbonitrile (0.818 g, 3.57 mmol) in DMSO (18 mL) in a round bottom flask, then add K2CO3 (0.247 g, 1.78 mmol). Cool the reaction flask in a water bath and add 30% H2O, (0.81 mL, 7.14 mmol) solution. After one hour, add water (25 mL). Filter the resulting precipitate and wash the filter cake with water (25 mL). Collect the filter cake as the title compound: HRMS calcd for C12H10NO3S 248.0381 (M+H)+, found 248.0396, time 0.36 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=13.0 min, 100% purity.