Ammonia → HCID 21431227, compound

HRID 436743Notes

Reaction equation

HRID 436743 reaction equation
[C:1]([N:5]=[N:6][C:7]1([N:13]=[C:14]=[S:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[NH3:16].C(=O)=O.O>CO>[C:1]([N:5]=[N:6][C:7]1([NH:13][C:14]([NH2:16])=[S:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 222Ammonia3×HCID 280Carbon DioxideHCID 962WaterHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexane

Product 1

HCID 21431227HCID 21431227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.4 grams (0.032 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane in 80 ml of methanol in a 250 ml reaction flask equipped with magnetic stirrer, thermometer, dry-ice condenser and gas addition tube was added NH3 gas until an NH3 reflux was obtained in the condenser. The reaction mixture was stirred for 3 hours at room temperature while maintaining a gentle NH3 reflux in the dry ice condenser. The reaction mixture was then poured into 200 ml of water and the product extracted with methylene chloride. The methylene chloride extract was washed with 10% NaHCO3 solution, water, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure. The residue was slurried in pentane and the slurry filtered. The white solid filter cake was air dried and weighed 4.5 grams (57% crude yield). The product melted at 155°-157° C. with decomposition. The infrared spectrum of the product contained a strong band at 1525 cm-1 and 3 NH bands at 3180, 3250 and 3400 cm-1.

Workup

  1. customequipped with magnetic stirrer
  2. additionthermometer, dry-ice condenser and gas addition tube
  3. temperaturereflux
  4. customwas obtained in the condenser
  5. extractionthe product extracted with methylene chloride
  6. extractionThe methylene chloride extract
  7. washwas washed with 10% NaHCO3 solution, water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe methylene chloride evaporated under reduced pressure
  11. filtrationthe slurry filtered
  12. filtrationThe white solid filter cake
  13. customdried

Sources & evidence

ORD record
ord-f027c200b6344b3b83571e7c80aa3b48
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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