Dimethylformamide dimethyl acetal → C20H17N3O3S

HRID 513830Notes

Reaction equation

HRID 513830 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-bc8de32d04b34894b20721182a3d6bf3
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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