Triethylamine → 1-ethoxycarbonyloxy-6-chloro1H-benzotriazole

HRID 596227Notes

Reaction equation

HRID 596227 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([O:4][C:2]([O:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 132928531-ethoxycarbonyloxy-6-chloro1H-benzotriazoleYield 45.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of ethyl chloroformate (2.17 g.) in benzene (10 ml.) was dropwise added to a solution of 1-hydroxy-6-chloro-1H-benzotriazole (3.38 g.) and triethylamine (2.80 ml.) in benzene (30 ml.) under ice-cooling and stirring. Benzene (30 ml.) was further added to the mixture and the reaction temperature was slowly elevated to room temperature, and the mixture was allowed to stand overnight. Precipitated crystals were filtered off and the filtrate was concentrated. Benzene was added to the residue and an insoluble material was filtered off, after which the filtrate was concentrated to give 1-ethoxycarbonyloxy-6-chloro-1H-benzotriazole (2.2 g.), crystal. These crystals, the precipitated crystals filtered off and the insoluble material in benzene were put together, in turn washed with water, a sodium bicarbonate aqueous solution, 1N hydrochloric acid and water, and recrystallized from methanol (75 ml.) to give the object compound (3.5 g.), white needles, mp 160° to 162° C.

Workup

  1. temperaturecooling
  2. customwas slowly elevated to room temperature
  3. customPrecipitated crystals
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated
  6. additionBenzene was added to the residue
  7. filtrationan insoluble material was filtered off
  8. concentrationafter which the filtrate was concentrated

Sources & evidence

ORD record
ord-dae3dd8a67704ba3b97ed42c6e992ee2
Source dataset
uspto-grants-1977_03
Patent number
US04010178

Reaction notes

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