Hydrochloric Acid → N-(tert-butyl)benzohydrazide

HRID 21652Notes

Reaction equation

HRID 21652 reaction equation
C(OC([NH:8][N:9]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([CH3:13])([CH3:12])[CH3:11])=O)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>CO>[C:10]([N:9]([C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH2:8])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15767552N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine

Product 1

HCID 1275961N-(tert-butyl)benzohydrazideYield 112.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mechanically stirred solution of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine (52 g, 0.18 mol) in methanol (100 ml) was added concentrated hydrochloric acid (35 ml). The resulting mixture was stirred at room temperature for 4 days and then neutralized with saturated aqueous sodium bicarbonate. The resulting white solid was filtered, washed with water and dried under vacuum to afford N'-t-butyl-N'-benzoylhydrazine (39 g): m.p. 124°-125° C.

Workup

  1. filtrationThe resulting white solid was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8ca370edf3534efdade178103671c44a
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Reaction notes

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