Ethanolamine → HCID 13255893, compound

HRID 268209Notes

Reaction equation

HRID 268209 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:18]([C:23](O)=[O:24])=[N:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:39]([CH2:41][NH2:42])[OH:40]>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:18]([C:23]([NH:42][CH2:41][CH2:39][OH:40])=[O:24])=[N:17]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12831724HCID 12831724, compound

Product 1

HCID 13255893HCID 13255893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3.76 parts of 1-(2-benzoyl-4-chlorophenyl)-5-chloromethyl-1H-1,2,4-triazole-3-carboxylic acid and 1.4 volume part of triethylamine in 60 volume parts of dry tetrahydrofuran, 1.0 volume part of ethyl chlorocarbonate is added dropwise under cooling with ice-salt. After 5 minutes, a solution of 1.2 volume part of ethanolamine in 10 volume parts of dry tetrahydrofuran is added dropwise to the mixture. After evaporation of the solvent below 40°C under reduced pressure, the residue is diluted with water. This procedure yields 1-(2-benzoyl-4-chlorophenyl)-5-chloromethyl-N-(2-hydroxyethyl)-1H-1,2,4-triazole-3-carboxamide as crystals. Recrystallization from ethanol gives colorless prisms melting at 170°-171°C.

Workup

  1. customAfter evaporation of the solvent below 40°C under reduced pressure
  2. additionthe residue is diluted with water

Sources & evidence

ORD record
ord-0f080b869d344583bda90de53b0bb7a4
Source dataset
uspto-grants-1976_03
Patent number
US03947417

Reaction notes

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