Ammonia → HCID 13798320, compound

HRID 580262Notes

Reaction equation

HRID 580262 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([Cl:16])[C:12]([CH3:17])=[N:11]1.[NH2-].[Na+].N.Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1.O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([Cl:16])[C:12]([CH3:17])=[N:11]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 7751Ethyl chloroacetateHCID 24533Sodium amideHCID 13798307HCID 13798307, compound

Product 1

HCID 13798320HCID 13798320, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,5-dimethyl-4-chloropyrazole (27.5 g) was dissolved in tetrahydrofuran (200 ml), and to the resultant solution was added sodium amide (4.0 g). When the evolution of ammonia gas from the reaction mixture ceased, ethyl monochloroacetate (12.3 g) was added dropwise to the reaction mixture. After the completion of addition, the reaction mixture was heated under reflux, with stirring for further 3 hours. To the reaction mixture, after cooling, were added toluene and water to form two layers. The organic layer as separated was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (33.9 g) as a pale brown crystalline solid. Recrystallization of this solid from cyclohexane afforded a white crystalline solid. m.p. 101°-104° C.

Workup

  1. additionAfter the completion of addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux
  4. temperatureTo the reaction mixture, after cooling
  5. customto form two layers
  6. customThe organic layer as separated
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customRemoval of the solvent
  10. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-57293f45a28f4d8ab78cfeb92833087f
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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