Nitric Acid → Diclopentezol

HRID 1200233

Reaction equation

HRID 1200233 reaction equation
C[C@@H](N)C(O)C1C=CC=CC=1.Cl.[BH4-].[Na+].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH:23]=[C:24]([N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)[C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].[N+]([O-])(O)=O>ClC1C=CC=CC=1.CN(C)C=O>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH:23]=[C:24]([N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)[CH:25]([OH:30])[C:26]([CH3:27])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 198220(2R)-2-amino-1-phenylpropan-1-ol;hydrochlorideHCID 4311764Sodium borohydrideHCID 540307821-(2,4-Dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl1-penten-3-one

Product 1

HCID 91738DiclopentezolYield 100.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

To d-norephedrine hydrochloride (832 g) and monochlorobenzene (2,343 g), a dimethylformamide solution of sodium borohydride (166 g) was added, and the resultant mixture was stirred at a temperature of 20° to 30° C. for 1 hour. A monochlorobenzene solution of the E isomer of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl1-penten-3-one (991 g) was added thereto, followed by stirring at the same temperature as above for 10 hours. The reaction mixture was treated with dilute nitric acid. The monochlorobenzene layer was separated and concentrated to give the E isomer of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol (1,000 g) (content, 97.0%; yield, 97.0%).

Workup

  1. customThe monochlorobenzene layer was separated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-13c346453b1344d8b00b96497f1e5aa2
Source dataset
uspto-grants-1990_02
Patent number
US04904793

Linked notes

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