Aniline → HCID 53862970, compound

HRID 436765Notes

Reaction equation

HRID 436765 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([C:17]([N:21]=[C:22]=[O:23])([CH2:19][CH3:20])[CH3:18])=[N:9][C:10]([N:14]=[C:15]=[O:16])([CH2:12][CH3:13])[CH3:11]>CCCCC>[N:8]([C:17]([NH:21][C:22]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:23])([CH2:19][CH3:20])[CH3:18])=[N:9][C:10]([NH:14][C:15]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16])([CH2:12][CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 6115AnilineHCID 53785527HCID 53785527, compound

Product 1

HCID 53862970HCID 53862970, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a stirred solution of 4.44 grams (0.0476 moles) of aniline in 30 ml of pentane in a 50 ml erlenmeyer flask cooled in a water bath was added 5.33 grams (0.0236 moles) of 2,2'-azobis (2 -isocyanatobutane) (from Example XXXVI) dropwise over 20 minutes while holding the reaction temperature below 30° C. After the addition was complete, the reaction was stirred for an additional 60 minutes at room temperature and filtered. The filter cake was washed with pentane and dried. The dry white solid weighed 1.5 grams (15% crude yield) and melted at 118°-120° C. The product had a strong carbonyl band at 1680 cm-1 and NH peaks at 3220 and 3420 cm-1 in its infrared spectrum and there was no isocyanate band at 2200 cm-1.

Workup

  1. customthe reaction temperature below 30° C
  2. additionAfter the addition
  3. filtrationfiltered
  4. washThe filter cake was washed with pentane
  5. customdried

Sources & evidence

ORD record
ord-821fc30c4c8f45cdb028edcf30854cda
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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