Dimethylformamide dimethyl acetal → C20H17N3O3S

HRID 74443Notes

Reaction equation

HRID 74443 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[C:19]2[C:27](=[O:31])[CH2:28][C:29]#[N:30])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[C:19]2[C:27]([C:28](=[CH:3][N:4]([CH3:5])[CH3:6])[C:29]#[N:30])=[O:31])(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 680047663-(1-benzenesulfonyl-1H-indol-2-yl)-3-oxo-propionitrile

Product 1

HCID 68005415C20H17N3O3S

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylformamide dimethylacetal (620 μl) was added at room temperature to a tetrahydrofuran (THF) solution (8.5 ml) of 3-(1-benzenesulfonyl-1H-indol-2-yl)-3-oxo-propionitrile (1.0 g, 3.08 mmol), and stirred for ten minutes. The reaction mixture was then concentrated under reduced pressure to give crude 2-(1-benzenesulfonyl-1H-indole-2-carbonyl)-3-dimethylamino-acrylonitrile as yellow amorphous material. The obtained crude product was used in subsequent reactions without purification.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give crude 2-(1-benzenesulfonyl-1H-indole-2-carbonyl)-3-dimethylamino-acrylonitrile as yellow amorphous material
  3. customThe obtained crude product
  4. customwas used in subsequent reactions without purification

Sources & evidence

ORD record
ord-0f051598477e4d77b7a0cbba6ad7d3ff
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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