Phenylhydrazine → HCID 54007022, compound

HRID 436777Notes

Reaction equation

HRID 436777 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]([C:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[N:10][C:11]1([N:17]=[C:18]=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CCCCC>[N:9]([C:20]1([NH:26][C:27]([NH:8][NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)=[N:10][C:11]1([NH:17][C:18]([NH:8][NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 53902663HCID 53902663, compound

Product 1

HCID 54007022HCID 54007022, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

To a stirred solution of 4.52 grams (.041 moles) of phenylhydrazine in 25 ml of pentane in a 125 ml erlenmeyer flask cooled in an ice bath was slowly added a solution of 5.77 grams (.0205 moles) of 1,1'-azobis (1-isocyanatocyclohexane) (from Example XCI) in 25 ml of pentane. After the addition was complete, the reaction was stirred an additional 90 minutes at 0° to 5° C. and filtered. The filter cake was washed with cold pentane and air dried. The dry white powder weighed 5.7 grams (57% crude yield) and melted at 148°-151° C. with decomposition. The infrared spectrum of the product contained a strong broad carbonyl band at 1670-1700 cm-1 and NH peaks at 3200-3340 cm-1. The isocyanate band of the starting material at 2225 cm-1 was absent.

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. washThe filter cake was washed with cold pentane and air
  4. customdried

Sources & evidence

ORD record
ord-6c4671e1bfa14ce5acb1c35139aec0c1
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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