Triethylamine → HCID 13292854, compound

HRID 2082996Notes

Reaction equation

HRID 2082996 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-20240ea2fff7441983e55c4937ae44ca
Source dataset
uspto-grants-1978_04
Patent number
US04083848

Reaction notes

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