Toluene → N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine

HRID 21651Notes

Reaction equation

HRID 21651 reaction equation
[C:1]([NH:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-:14].[Na+].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.C(Cl)(=O)C1C=CC=CC=1>[C:10]([O:9][C:7]([NH:6][N:5]([C:22](=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([CH3:4])([CH3:3])[CH3:2])=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 3771477N'-t-Butyl(tert-butoxy)carbohydrazide

Product 1

HCID 15767552N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7412Benzoyl chlorideSolvent

Procedure

A mechanically stirred solution of N'-t-butyl-N-t-butoxycarbonylhydrazine (61 g, 0.32 mol) in toluene (120 ml) cooled in an ice bath, was treated dropwise and simultaneously with 50% sodium hydroxide (31 g) in water (50 ml) and benzoyl chloride (45 g). The addition was complete in 20 minutes and the resulting mixture was warmed to room temperature and allowed to stir for 1 hour. The resulting white solid was filtered, washed with water and air dried to afford 94 g of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine: m.p. 167°-170° C.

Workup

  1. additionThe addition
  2. filtrationThe resulting white solid was filtered
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-90b2744343d74aed85d93b84af0d1f06
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Reaction notes

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