Triethylamine → HCID 13292854, compound

HRID 597693Notes

Reaction equation

HRID 597693 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.C(N(CC)CC)C>C1C=CC=CC=1.O>[CH2:5]([O:4][C:2]([O:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 13292854HCID 13292854, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Benzyl chloroformate (8.5 g.) was added dropwise under ice-cooling to a solution of 1-hydroxy-1H-benzotriazole (6.8 g.) and triethylamine (7.0 ml.) in a mixture of benzene (100 ml.) and water (50 ml.), and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was filtered and the precipitated crystals were washed with water and dried. The benzene layer was washed with water, dried and concentrated. The residue and the crystals obtained above were mixed and recrystallized from a mixed solvent of benzene and petroleum ether to give 1-benzyloxycarbonyloxy-1H-benzotriazole (12.1 g.), mp 130° to 131° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitated crystals were washed with water
  3. customdried
  4. washThe benzene layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue and the crystals obtained
  8. additionabove were mixed
  9. customrecrystallized from a mixed solvent of benzene and petroleum ether

Sources & evidence

ORD record
ord-06c714ff81b743d48d39e98704704e98
Source dataset
uspto-grants-1977_03
Patent number
US04014915

Reaction notes

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