Dimethylformamide → HCID 19860705, compound

HRID 868410Notes

Reaction equation

HRID 868410 reaction equation
CS([CH2:5][C:6]([F:10])([F:9])[CH:7]=[CH2:8])(=O)=O.[C:11]1([C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][O:13]1)=[O:12].[K].C[N:23](C)C=O>>[C:14]1(=[O:13])[N:23]([CH2:5][C:6]([F:10])([F:9])[CH:7]=[CH2:8])[C:11](=[O:12])[C:20]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:15]12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 19860699HCID 19860699, compoundHCID 67006573Potassium phthalide

Product 1

HCID 19860705HCID 19860705, compound

Conditions

Temperature
110 °C

Procedure

The compound 1-methanesulfonyl-2,2-difluoro-3-butene (11.2 g, 60.2 mM), potassium phthalide (12.3 g, 66.4 mM) and dry dimethylformamide (30 mL) are stirred and heated (bath temperature 110° C.) under nitrogen for 120 hours. After cooling to room temperature, the crude reaction product is precipitated by the addition of water (approximately 300 mL), filtered and dissolved in dichloromethane. The dichloromethane solution is washed with 1N potassium hydroxide (twice), water (twice), dried (Na2SO4) and evaporated to yield 1-phthalimido-2,2-difluoro-3-butene as beige-colored crystals: 11.9 g (83%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe crude reaction product
  3. customis precipitated by the addition of water (approximately 300 mL)
  4. filtrationfiltered
  5. dissolutiondissolved in dichloromethane
  6. washThe dichloromethane solution is washed with 1N potassium hydroxide (twice), water (twice),
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-2199ddd4bd2641bf8931db784d2a0a56
Source dataset
uspto-grants-1988_10
Patent number
US04778926

Reaction notes

Loading…