Dimethylformamide → HCID 19828097, compound

HRID 1494424Notes

Reaction equation

HRID 1494424 reaction equation
[OH:1][C:2]1[C:12]([O:13][CH3:14])=[CH:11][C:5]2[S:6][C:7]([C:9]#[N:10])=[CH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH:27]([F:29])[F:28]>O>[F:28][CH:27]([F:29])[O:1][C:2]1[C:12]([O:13][CH3:14])=[CH:11][C:5]2[S:6][C:7]([C:9]#[N:10])=[CH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 19828133HCID 19828133, compound

Product 1

HCID 19828097HCID 19828097, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-hydroxy-6-methoxy-benzo[b]thiophene-2-carbonitrile (10.30 g) and anhydrous potassium carbonate (7.63 g) was treated with a solution of dry dimethylformamide (110 ml) which has been previously saturated with chlorodifluoromethane gas. The mixture was then sealed in an autoclave, stirred, and heated to 40° C. After 3 days the reaction mixture was cooled and poured into water (700 ml). The resultant precipitate was iiltered off, dried, and extracted with hot dichloromethane (300 ml). The organic extract was concentrated then poured through a column of fine silica (200 g). The appropiate fractions were combined and evaporated to dryness to give 5-difluoromethyloxy-6-methoxy-benzo[b]thiophene-2-carbonitrile as an off-white solid (5.49 g), m.p. 99°-101° C.

Workup

  1. customThe mixture was then sealed in an autoclave
  2. temperatureAfter 3 days the reaction mixture was cooled
  3. customdried
  4. extractionextracted with hot dichloromethane (300 ml)
  5. extractionThe organic extract
  6. concentrationwas concentrated
  7. additionthen poured through a column of fine silica (200 g)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-41d0af51a026411f9ddd620eda4b8561
Source dataset
uspto-grants-1991_06
Patent number
US05026724

Reaction notes

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