Dimethylformamide dimethyl acetal → HCID 87203411, compound

HRID 2242039Notes

Reaction equation

HRID 2242039 reaction equation
[OH:1][C:2]1[C:3]([S:15](=[O:18])(=[O:17])[NH2:16])=[C:4]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH3:21][N:22]([CH3:24])/[CH:23]=[N:16]/[S:15]([C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66916062HCID 66916062, compound

Product 1

HCID 87203411HCID 87203411, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-hydroxy-2-sulfamoyl-phenyl)-2,2-dimethyl-propionamide (15.2 g, 55.9 mmol) and N,N-dimethylformamide dimethylacetal (9.7 ml, 72.6 mmol) in DMF (65 ml) is stirred at 60° C. for 1 h. Volatiles are evaporated at reduced pressure. Chromatography of the residue (21.8 g) dissolved in dichloromethane (silica gel, hexanes/EtOAc=1:1) gives N-(2-{[1-dimethylamino-meth-(E)-ylidene]-sulfamoyl}-3-hydroxy-phenyl)-2,2-dimethyl-propionamide.

Workup

  1. customVolatiles are evaporated at reduced pressure
  2. dissolutionChromatography of the residue (21.8 g) dissolved in dichloromethane (silica gel, hexanes/EtOAc=1:1)

Sources & evidence

ORD record
ord-d1ceeb3f17f3459d9d71684b4f3f3c26
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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