Toluene → HCID 86745868, compound

HRID 1197261Notes

Reaction equation

HRID 1197261 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[C:19](Cl)(=[O:26])C1C=CC=CC=1.[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCCCCC>[C:2]([N:6]([C:16](=[O:17])[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=[C:19]=[O:26])[NH:7][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 1140Toluene2×HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide3×HCID 75938Cyclohexanecarbonyl chlorideHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 86745868HCID 86745868, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexanecarbonylchloride (2.4 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.5 g, 0.008M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (1.1 g, 0.008M) and 50% sodium hydroxide (0.6 g, 0.008M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexylcarbonyl-N'-benzyylhydrazine, isolated by filtration.

Workup

  1. temperaturesimultaneously so as to maintain the reaction temperature below 10° C
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customthe solid product isolated by filtration
  5. temperaturecooled on ice
  6. additionAfter addition
  7. stirringthe mixture was stirred for 1/2 hr
  8. customthe solid product, N'-t-butyl-N-cyclohexylcarbonyl-N'-benzyylhydrazine, isolated by filtration

Sources & evidence

ORD record
ord-a66ffc299f264dee9eae6904750f9e9b
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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