Toluene → N'-t-butyl-N-pyrenonecarbonyl-N'-(3-toluoyl)hydrazine

HRID 1197299Notes

Reaction equation

HRID 1197299 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[C:8]1(=[O:27])[C:21]2[C:22]3=[C:23]4[C:18](=[CH:19][CH:20]=2)[CH:17]=[CH:16][CH:15]=[C:14]4[CH:13]=[CH:12][C:11]3=[CH:10][CH:9]1[C:24](Cl)=[O:25].CC[O:30][CH2:31][CH3:32].CCCCCC.[C:39]1([CH3:45])[CH:44]=C[CH:42]=[CH:41][CH:40]=1>[OH-]>[C:2]([N:6]([C:31]([C:32]1[CH:44]=[C:39]([CH3:45])[CH:40]=[CH:41][CH:42]=1)=[O:30])[NH:7][C:24]([CH:9]1[CH:10]=[C:11]2[C:22]3=[C:23]4[C:18]([CH:17]=[CH:16][CH:15]=[C:14]4[CH:13]=[CH:12]2)=[CH:19][CH:20]=[C:21]3[C:8]1=[O:27])=[O:25])([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 1140TolueneHCID 3283Diethyl EtherHCID 8058HexaneHCID 81889tert-Butylhydrazine monohydrochlorideHCID 131717420Pyrenonecarbonyl chloride

Product 1

HCID 131717419N'-t-butyl-N-pyrenonecarbonyl-N'-(3-toluoyl)hydrazine

Reagents, catalysts & solvents 1

HCID 961HydroxideSolvent

Procedure

To a stirred suspension of t-butyl hydrazine hydrochloride (0.02 mol) in toluene (20 ml) and aqueous hydroxide (5 ml of 50% solution) at room temperature was added pyrenonecarbonyl chloride (0.01 mol). After stirring the reaction mixture for 20 minutes, ether and hexane were added and the solid product was filtered and washed with water. The solid product (0.5 g) was stirred in toluene (10 ml) and aqueous sodium hydroxide and m-toluoyl chloride (0.8 g) was added dropwise. After stirring for 5 hours, hexane and ether were added and the solid product filtered and air dried.

Workup

  1. filtrationthe solid product was filtered
  2. washwashed with water
  3. stirringThe solid product (0.5 g) was stirred in toluene (10 ml)
  4. additionaqueous sodium hydroxide and m-toluoyl chloride (0.8 g) was added dropwise
  5. stirringAfter stirring for 5 hours
  6. additionhexane and ether were added
  7. filtrationthe solid product filtered
  8. customair dried

Sources & evidence

ORD record
ord-bb48e46cbefe494b8441eaae727adf0e
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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