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

HRID 747551Notes

Reaction equation

HRID 747551 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

5

Reactant 3

HCID 962Water2×HCID 11430Potassium CarbonateHCID 586773735-(4-Formylphenoxy)thiophene-2-carbonitrile

Product 1

HCID 586773915-(4-Formylphenoxy)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. temperatureCool the reaction flask in a water bath
  2. filtrationFilter the resulting precipitate
  3. washwash the filter cake with water (25 mL)
  4. customCollect the filter cake as the title compound
  5. custom248.0396, time 0.36 min
  6. customHPLC [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

Sources & evidence

ORD record
ord-c37712cba5734d42ae0f99e4f874d7bb
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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