Ammonia → HCID 13561854, compound

HRID 979405Notes

Reaction equation

HRID 979405 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][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].N1C=CC=CC=1.N>C(Cl)(Cl)Cl.C(O)C>[C:24]([C:8]1[CH:9]=[N:10][N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:21])([F:22])[F:20])=[CH:14][C:13]=2[Cl:23])[C:7]=1[NH:6][C:1](=[O:4])[CH2:2][CH3:3])#[N:25]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 62324Propionyl chlorideHCID 135618335-Amino-4-cyano-1-(2-chloro-4-trifluoromethoxy-phenyl)-pyrazole

Product 1

HCID 13561854HCID 13561854, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Procedure

10 ml (0.11 mole) of propionyl chloride are added to 2.9 g (0.01 mole) of 5-amino-4-cyano-1-(2-chloro-4-trifluoromethoxy-phenyl)-pyrazole in 30 ml of chloroform at 0° C., with stirring, and a solution of 1.8 ml (0.02 mole) of pyridine in 15 ml of chloroform is then added, also at 0° C. When the addition has ended, stirring is continued at room temperature for 20 hours, the solvent is stripped off, the residue is taken up in 50 ml of ethanol, aqueous ammonia is added until the reaction is alkaline, the volatile constituents are removed in vacuo, the residue is taken up in 100 ml of chloroform, the mixture is washed with water, then with 2N aqueous hydrochloric acid and again with water and dried over sodium sulphate and the solvent is removed in vacuo. 2.7 g (75.3% of theory) of 4-cyano-1-(2-chloro-4-trifluoromethoxy-phenyl)-5-propionylamino-pyrazole of melting point 127° C. are obtained.

Workup

  1. additionWhen the addition
  2. stirringstirring
  3. customthe volatile constituents are removed in vacuo
  4. washthe mixture is washed with water
  5. dry with materialwith 2N aqueous hydrochloric acid and again with water and dried over sodium sulphate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9609ae51f0e64e44a62bf13633202487
Source dataset
uspto-grants-1987_05
Patent number
US04668280

Reaction notes

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