Sodium Hydroxide → (-)-6-[(4-chlorophenyl)hydrazinomethyl]-1methyl-1H-benzotriazole

HRID 1376822Notes

Reaction equation

HRID 1376822 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>ClCCl.O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18924324(+)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride

Product 1

HCID 18924312(-)-6-[(4-chlorophenyl)hydrazinomethyl]-1methyl-1H-benzotriazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8.1 g of intermediate 2-b in 60 ml of dichloromethane was added a solution of 1 g sodium hydroxide in 15 ml of water. The whole was stirred for 15 min., then the organic layer was separated and evaporated. The residue and 1.4 g of potassium hydroxide were refluxed in 50 ml ethanol for 3 hours, yielding (-)-6-[(4-chlorophenyl)hydrazinomethyl]-1methyl-1H-benzotriazole (interm. 2-c); enantiomeric excess: 20%.

Workup

  1. customthe organic layer was separated
  2. customevaporated
  3. temperatureThe residue and 1.4 g of potassium hydroxide were refluxed in 50 ml ethanol for 3 hours

Sources & evidence

ORD record
ord-960d6792c16446209bd33f5202babe93
Source dataset
uspto-grants-1997_09
Patent number
US05663354

Reaction notes

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