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

HRID 1288621Notes

Reaction equation

HRID 1288621 reaction equation
[ClH:1].ClC1C=CC([CH:9]([NH:20][NH2:21])[C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[N:16][N:15]([CH3:18])[C:14]=3[CH:19]=2)=CC=1.[OH-].[Na+]>ClCCl.O>[Cl:1][C:10]1[CH:11]=[CH:12][C:13]([NH:21][NH:20][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[N:16][N:15]([CH3:18])[C:14]=3[CH:19]=2)=[CH:14][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18924309(-)-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]-1-methyl-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-61808bd61e0c4951bd74b0eb2dc32d2e
Source dataset
uspto-grants-1998_05
Patent number
US05746840

Reaction notes

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