Sodium Hydroxide → N'-t-butyl-N-(beta-chloropivaloyl)-N'-benzoylhydrazine

HRID 21636

Reaction equation

HRID 21636 reaction equation
[C:1]([N:5]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6])([CH3:4])([CH3:3])[CH3:2].[Cl:15][CH2:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].[OH-].[Na+]>C1(C)C=CC=CC=1.CCCCCC.O>[C:1]([N:5]([C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:6][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH2:16][Cl:15])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 1275961N-(tert-butyl)benzohydrazide

Product 1

HCID 19367896N'-t-butyl-N-(beta-chloropivaloyl)-N'-benzoylhydrazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1 g, 0.005M) in toluene (40 ml) cooled to 5° C. was added 3-chloro-2,2-dimethylpropionylchloride (1.2 g, 0.007M) and 50% aq. sodium hydroxide (0.45 g, 0.0056M) so as to maintain the temperature below 10° C. The mixture was warmed to room temperature and stirred 1 hour. The mixture was diluted with hexane (40 ml) and water (10 ml). The white solid product N'-t-butyl-N-(beta-chloropivaloyl)-N'-benzoylhydrazine was isolated by suction filtration, washed with 50 ml hexane and 50 ml water and dried.

Workup

  1. temperatureto maintain the temperature below 10° C

Sources & evidence

ORD record
ord-e9168985485e4f87a15b73f20277f974
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

Loading…