Acetyl chloride → HCID 13127639, compound

HRID 1462141Notes

Reaction equation

HRID 1462141 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([F:14])=[C:9]([F:15])[C:8]=2[F:16])[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[H-].[Na+].[H][H].[C:23](Cl)(=[O:25])[CH3:24].[O:27]1CC[CH2:29][CH2:28]1>>[C:17]([C:3]1[CH:4]=[N:5][N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([F:14])=[C:9]([F:15])[C:8]=2[F:16])[C:2]=1[N:1]([C:28](=[O:27])[CH3:29])[C:23](=[O:25])[CH3:24])#[N:18]

Participants

6

Reactant 5

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 12952970HCID 12952970, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13127639HCID 13127639, compound

Procedure

A solution of 5-amino-4-cyano-1-(2,3,4,6-tetrafluorophenyl)pyrazole (2.6 g; described in British Published Patent Specification No. 2,070,604A.) in dry tetrahydrofuran (10 ml) was added dropwise to a stirred suspension of powdered sodium hydride (0.53 g) in dry tetrahydrofuran, under nitrogen, at a temperature not exceeding 30° C. maintained by external cooling (ice). When the evolution of hydrogen had ceased a solution of acetyl chloride (1.5 ml) in tetrahydrofuran (15 ml) was added at a temperature not exceeding 30° C. After stirring at laboratory temperature for 48 hours the reaction mixture was washed with saturated aqueous ammonium chloride and the organic layer separated and dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was chromatographed on a silica column (Merck 230-400 mesh; 10 lb in-2) using dichloromethane as eluent. Evaporation of the eluate containing the major component gave a solid which was crystallised from a mixture of toluene and hexane to give 4-cyano-5-diacetylamino-1-(2,3,4,6-tetrafluorophenyl)-pyrazole (1.5 g), m.p. 132°-134° C., in the form of colourless crystals.

Workup

  1. customexceeding 30° C.
  2. temperaturemaintained
  3. temperatureby external cooling (ice)
  4. additionwas added at a temperature not
  5. customexceeding 30° C
  6. washwas washed with saturated aqueous ammonium chloride
  7. customthe organic layer separated
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated to dryness
  10. customThe residue was chromatographed on a silica column (Merck 230-400 mesh; 10 lb in-2)
  11. customEvaporation of the eluate
  12. additioncontaining the major component
  13. customgave a solid which
  14. customwas crystallised from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-c45e99439c194b36958b06e774d81edb
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

Loading…