Water → HCID 178425304, compound

HRID 1461566Notes

Reaction equation

HRID 1461566 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([N:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[NH2:8])=[O:6].[OH-].[Na+].[C-:18]1([C:23](Cl)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19]1.[CH-:26]1[CH:30]=[CH:29][CH:28]=[CH:27]1.[Fe+2:31].O>C1(C)C=CC=CC=1>[C-:18]1([C:23]([NH:8][N:7]([C:5](=[O:6])[C:4]2[CH:13]=[CH:14][CH:15]=[C:2]([CH3:1])[CH:3]=2)[C:9]([CH3:12])([CH3:10])[CH3:11])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19]1.[CH-:26]1[CH:30]=[CH:29][CH:28]=[CH:27]1.[Fe+2:31]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15452040N'-t-butyl-N'-(3-methylbenzoyl)hydrazineHCID 178521103HCID 178521103, compound

Product 1

HCID 178425304HCID 178425304, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of N'-3-methylbenzoyl-N'-t-butylhydrazine (0.83 g, 4.0 mmol) and 50% aqueous sodium hydroxide (0.4 g, 5.0 mmol) in toluene (30 mL) was added 7 mL of a toluene solution of ferrocenoyl chloride (Example 2), at room temperature dropwise (addition time 2 hours). After the addition was completed water is added (5 mL) and the resulting mixture allowed to stand overnight, filtered and the filtrate washed with water and dried over MgSO4. Evaporation of the solvent yielded a brown oil which crystalized after rituration with hexane. N-ferrocenoyl-N'-3-methylbenzoyl-N'-t-butylhydrazine was obtained as a brown solid mp: 181°-184° C.

Workup

  1. additionat room temperature dropwise (addition time 2 hours)
  2. additionAfter the addition
  3. additionis added (5 mL)
  4. filtrationfiltered
  5. washthe filtrate washed with water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent
  8. customyielded a brown oil which
  9. customcrystalized after rituration with hexane

Sources & evidence

ORD record
ord-25c730c9132c475abce04bea553c12cc
Source dataset
uspto-grants-1991_12
Patent number
US05075471

Reaction notes

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