Ethylamine → HCID 13281520, compound

HRID 1249124Notes

Reaction equation

HRID 1249124 reaction equation
Cl[C:2]([CH2:4][NH:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[Cl:21])[N:9]=[CH:8][C:7]=1[C:22]#[N:23])=[O:3].[CH2:24]([NH2:26])[CH3:25]>C(C(C)=O)C>[Cl:21][C:12]1[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=1[N:10]1[C:6]([NH:5][CH2:4][C:2]([NH:26][CH2:24][CH3:25])=[O:3])=[C:7]([C:22]#[N:23])[CH:8]=[N:9]1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 13281512HCID 13281512, compound

Product 1

HCID 13281520HCID 13281520, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of 5-chlorocarbonylmethylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (4.72 g) in dry methyl ethyl ketone (25 ml) was added over 5 minutes to a stirred solution of ethylamine (20 ml) in methyl ethyl ketone (100 ml) at 0° C. (maintained by external cooling). The resulting suspension was stirred for 1 hour whilst the reaction mixture attained laboratory temperature. The reaction mixture was evaporated to dryness and the residue was dissolved in a mixture of diethyl ether (100 ml) and water (100 ml). After separation of the organic layer, the organic layer was washed successively with aqueous 2N hydrochloric acid (2×100 ml) and water (3×50 ml) and dried over anhydrous sodium sulphate. Evaporation of the solution to dryness gave a fawn coloured powder (3.6 g. m.p. 144°-145° C.) which was chromatographed using dichloromethane-ethyl acetate (4:1) as eluent. Evaporation of the eluate containing the major component gave a yellow oil which was crystallised from a mixture of toluene (5 ml) and hexane (40 ml) to give 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-ethylaminocarbonylmethylaminopyrazole, m.p. 150°-151° C. in the form of colourless crystals.

Workup

  1. temperature(maintained by external cooling)
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in a mixture of diethyl ether (100 ml) and water (100 ml)
  4. customAfter separation of the organic layer
  5. washthe organic layer was washed successively with aqueous 2N hydrochloric acid (2×100 ml) and water (3×50 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. customEvaporation of the solution to dryness
  8. customgave a fawn
  9. customwas chromatographed
  10. customEvaporation of the eluate
  11. additioncontaining the major component
  12. customgave a yellow oil which
  13. customwas crystallised from a mixture of toluene (5 ml) and hexane (40 ml)

Sources & evidence

ORD record
ord-7ce5692829cb4afeb95efb5330f7e548
Source dataset
uspto-grants-1986_12
Patent number
US04629495

Reaction notes

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