Dimethyl Sulfoxide → HCID 18976173, compound

HRID 2393609Notes

Reaction equation

HRID 2393609 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.Cl.[NH2:16][CH:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[N:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[C:18]1=[O:35]>O>[NH2:16][C:17]1([CH2:3][CH2:2][C:1]#[N:4])[C:25]2[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[N:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[C:18]1=[O:35]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7855AcrylonitrileHCID 11430Potassium CarbonateHCID 18976153HCID 18976153, compound

Product 1

HCID 18976173HCID 18976173, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon gas atmosphere, 29.90 ml of acrylonitrile and 62.70 g of potassium carbonate were added to 210 ml of a dimethyl sulfoxide solution of 70.00 g of 3-amino-1-(2-fluorophenyl)-2,3-dihydro-6-methoxy-1H-indol-2-one hydrochloride, and the whole was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate extract was washed with water successively with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate and then filtered. The filtrate was evaporated to afford 70.70 g of 3-[3-amino-1-(2-fluorophenyl)-2,3-dihydro-6-methoxy-2-oxo-1H-indol-3-yl]propanenitrile as a brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water successively with water
  4. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-523edcee5c8040d0aca3b3d00895fea6
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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