Benzoyl chloride → N'-t-butyl-N-(2-hydroxymethylbenzoyl)-N'-benzoylhydrazine

HRID 1197249Notes

Reaction equation

HRID 1197249 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[Na+]>[C:1]([N:5]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 19368051N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine

Product 1

HCID 19367869N'-t-butyl-N-(2-hydroxymethylbenzoyl)-N'-benzoylhydrazineYield 58.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.7 g of N'-t-butyl-N-(2-hydroxymethylbenzoyl)-hydrazine and 1.1 g benzoyl chloride are combined in 10 ml of 5% NaOH and stirred at room temperature for 1.5 hours. The solids are filtered off, washed with water, then ether, to afford 0.6 g of white solid N'-t-butyl-N-(2-(benzoyloxymethyl)benzoyl)-N'-benzoylhydrazine. m.p. 190°-191° C.

Workup

  1. filtrationThe solids are filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-104e7490d8f14a38b087ec033a8d6352
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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