Ammonia → HCID 13255888, compound

HRID 268208Notes

Reaction equation

HRID 268208 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21][Cl:22])=[N:19]C(C(O)=O)=[N:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:28](CC)CC)C.C(Cl)(=O)[O:34][CH2:35][CH3:36].N>O.O1CCCC1>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21][Cl:22])=[N:19][C:36]([C:35]([NH2:28])=[O:34])=[N:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12831724HCID 12831724, compound

Product 1

HCID 13255888HCID 13255888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under cooling with ice and stirring, to a solution of 7.5 parts of 1-(2-benzoyl-4-chlorophenyl)-5-chloromethyl-1H-1,2,4-triazole-3-carboxylic acid and 2.8 volume parts of triethylamine in 100 volume parts of dry tetrahydrofuran, 2.0 volume parts of ethyl chlorocarbonate is added dropwise. The solution is then added dropwise to 200 volume parts of ice-cooled concentrated aqueous ammonia (28 %). After stirring for 10 minutes, the mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate layer is washed with water and the solvent is distilled off. The residue is treated with ether to obtain 1-(2-benzoyl-4-chlorophenyl)-5-chloromethyl-1H-1,2,4-triazole-3-carboxamide as crystals. Recrystallization from ethanol gives colorless crystals melting at 122°-124°C (this product includes 1/2 ethanol of crystallization).

Workup

  1. temperatureUnder cooling with ice
  2. additionis added dropwise
  3. additionThe solution is then added dropwise to 200 volume parts of ice-
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer is washed with water
  6. distillationthe solvent is distilled off
  7. additionThe residue is treated with ether

Sources & evidence

ORD record
ord-db286286e8f84967ae44149cb801ac0a
Source dataset
uspto-grants-1976_03
Patent number
US03947417

Reaction notes

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