Ethyl chloroformate → HCID 10183087, compound

HRID 842159Notes

Reaction equation

HRID 842159 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[N:12]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:11]=[C:10]([C:25]([F:28])([F:27])[F:26])[C:9]=1[C:29]#[N:30]>N1C=CC=CC=1>[C:29]([C:9]1[C:10]([C:25]([F:28])([F:26])[F:27])=[N:11][N:12]([C:13]2[C:14]([Cl:24])=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])=[CH:17][C:18]=2[Cl:19])[C:8]=1[NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])#[N:30]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformate2×HCID 101349005-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 10183087HCID 10183087, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (1.6 g) was added to a stirred solution of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (3.9 g) in pyridine (15 ml). After stirring overnight another addition of ethyl chloroformate (1.0 ml) was made, and the mixture was left for a further 12 hours. The solvent was evaporated in vacuo and the residue was acidified with dilute hydrochloric acid, and extracted with dichloromethane. This extract was washed with water (3×), dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo. Purification by chromatography on silica (Merck, 40-230 mesh, 0.7 kg cm−2) eluting with ethyl acetate-petroleum ether (1:1) gave a white solid, which was recrystallized from a mixture of dichloromethane and hexane to furnish white crystals of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxycarbonylamino-3-trifluoromethylpyrazole, m.p. 177-179° C.

Workup

  1. waitthe mixture was left for a further 12 hours
  2. customThe solvent was evaporated in vacuo
  3. extractionextracted with dichloromethane
  4. washThis extract was washed with water (3×)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification by chromatography on silica (Merck, 40-230 mesh, 0.7 kg cm−2)
  9. washeluting with ethyl acetate-petroleum ether (1:1)
  10. customgave a white solid, which
  11. customwas recrystallized from a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-3ee42177379a43e5acb2087e45028633
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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