Sodium hydride → HCID 13281595, compound

HRID 1249126Notes

Reaction equation

HRID 1249126 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:10]=[CH:9][C:8]=1[C:24]#[N:25])=[O:5].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.ClCCl>[C:24]([C:8]1[CH:9]=[N:10][N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:21])([F:22])[F:20])=[CH:14][C:13]=2[Cl:23])[C:7]=1[N:6]1[CH2:2][CH2:3][C:4]1=[O:5])#[N:25]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13281605HCID 13281605, compound

Product 1

HCID 13281595HCID 13281595, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(3-chloropropionamido)-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (4.12 g) in a mixture of dimethylformamide (20 ml) and dichloromethane (80 ml) was added dropwise over 6 hours to a rapidly stirred suspension of powdered sodium hydride (0.30 g) in a mixture of dimethylformamide (20 ml) and dichloromethane (80 ml) at laboratory temperature. The reaction mixture was then stirred for 24 hours. After standing at laboratory temperature for 48 hours, saturated aqueous ammonium chloride solution was added. The organic layer was removed, washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was chromatographed using diethyl ether-hexane (1:1) as eluent. Evaporation of the eluate containing the faster moving component gave 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(2-oxo-azetidin-1-yl)pyrazole (1.40 g), m.p. 162°-164° C., in the form of a colourless solid.

Workup

  1. waitAfter standing at laboratory temperature for 48 hours
  2. customThe organic layer was removed
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness
  6. customThe residue was chromatographed
  7. customEvaporation of the eluate
  8. additioncontaining the

Sources & evidence

ORD record
ord-0fb721278d35499c9920e7b4010e1a21
Source dataset
uspto-grants-1986_12
Patent number
US04629495

Reaction notes

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