Ammonia → HCID 21431125, compound

HRID 436752Notes

Reaction equation

HRID 436752 reaction equation
[C:1]([N:5]=[N:6][C:7]1([N:13]=[C:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].N.O.[N-:18]=C=O>CO>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH2:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 962WaterHCID 105034IsocyanateHCID 214311721-t-Butylazo-1-isocyanatocyclohexane

Product 1

HCID 21431125HCID 21431125, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9.25 grams (0.0442 moles) of 1-t-butylazo-1-isocyanatocyclohexane in 50 ml of methanol in a 250 ml 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, gas addition tube and dry ice condenser was added gaseous ammonia until a gentle ammonia reflux was maintained in the condenser. The reaction was stirred for 90 minutes at room temperature, poured into 300 ml water and the solid that formed was filtered off. The filter cake was air dried leaving 9.0 grams (90% crude yield) of a white powder. The product melted at 115°-117° C. and its infrared spectrum contained a strong carbonyl band at 1670 cm-1 and sharp NH bands at 3250 cm-1 3330 cm-1 and 3440 cm-1. The isocyanate band at 2225 cm-1 was absent.

Workup

  1. additionthermometer, gas addition tube and dry ice condenser
  2. temperaturereflux
  3. temperaturewas maintained in the condenser
  4. customthe solid that formed
  5. filtrationwas filtered off
  6. customdried
  7. customleaving 9.0 grams (90% crude yield) of a white powder

Sources & evidence

ORD record
ord-193bd70c7e544251b2205e29b62c6a0c
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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