Dimethylformamide → HCID 70912774, compound

HRID 1053250Notes

Reaction equation

HRID 1053250 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[CH3:15][N:16]([CH:18]=O)[CH3:17].CN(C(OC)OC)C>C(OC(=O)C)C>[CH3:15][N:16]([CH3:18])[CH:17]=[N:14][S:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:10][CH:9]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 70209431HCID 70209431, compound

Product 1

HCID 70912774HCID 70912774, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-propionylbenzenesulfonamide (prepared according to the procedure reported in Bioorganic Chemistry 1994, 22, 387-394), 2.2 g (10.3 mmol) in ethylacetate (20 ml) was added DMF (2.0 ml) followed by the addition of N,N-dimethylformamidedimethyl acetal (1.36 g, 1.51 ml, 11.36 mmol) in a dropwise manner at room temperature. The resulting mixture was stirred at room temperature for 4 hr. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure to obtain a solid product, which was washed with diisopropylether to obtain the title compound (2.6 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto obtain a solid product, which
  3. washwas washed with diisopropylether

Sources & evidence

ORD record
ord-53d821adeda24871a352a9380bd5f18f
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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