Benzoylhydrazine → HCID 21431282, compound

HRID 436742Notes

Reaction equation

HRID 436742 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([N:15]=[N:16][C:17]1([N:23]=[C:24]=[S:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)([CH3:14])([CH3:13])[CH3:12].[N-]=C=S>CO>[C:11]([N:15]=[N:16][C:17]1([NH:23][C:24](=[S:25])[NH:10][NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11955BenzoylhydrazineHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexaneHCID 178418790HCID 178418790, compound

Product 1

HCID 21431282HCID 21431282, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.02 grams (0.0295 moles) of benzoylhydrazine in 25 ml of methanol in a 50 ml erlenmeyer flask was added 6.82 grams (0.0295 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane and the reaction mixture stirred for 6 days at room temperature. The methanol was evaporated under reduced pressure leaving a pale yellow solid weighing 9.0 grams (75% crude yield). The product melted with decomposition at 190°-193° C. The infrared spectrum of the product had amide bands at 1640 and 1690 cm-1, a strong band at 1550 cm-1 [-N(H)CS] and weak NH bands from 3100-3300 cm-1. The isothiocyanate band at 2040 cm-1 was absent.

Workup

  1. customThe methanol was evaporated under reduced pressure
  2. customleaving a pale yellow solid
  3. custommelted with decomposition at 190°-193° C

Sources & evidence

ORD record
ord-43d0f1728e894fb281cbcde9adfcb574
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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