Propyl isocyanate → HCID 13228803, compound

HRID 1648768Notes

Reaction equation

HRID 1648768 reaction equation
[OH:1][NH:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4].[CH2:8]([N:11]=[C:12]=[O:13])[CH2:9][CH3:10]>C(N(CC)CC)C.C(Cl)Cl>[CH2:8]([NH:11][C:12]([N:2]([O:1][C:12]([NH:11][CH2:8][CH2:9][CH3:10])=[O:13])[C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4])=[O:13])[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 61033Propyl isocyanateHCID 9989224N-Hydroxycyclopropanecarboximidic acid

Product 1

HCID 13228803HCID 13228803, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-hydroxycyclopropanecarboxamide (5.0 grams), n-propyl isocyanate (9.3 grams) and 5 drops of triethylamine were stirred at room temperature in about 100 ml of methylene chloride for about 12 hours. The reaction mixture was then concentrated leaving an oily residue which crystallized upon scratching. This solid was then recrystallized from a mixture of cyclohexane and isopropanol and dried. Upon drying, the desired N-((propylamino)carbonyl)-N-(((propylamino)carbonyl)-oxy)cyclopropanecarboxamide was obtained as a white solid, m.p. 76°-78° C.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customleaving an oily residue which
  3. customcrystallized
  4. customThis solid was then recrystallized from a mixture of cyclohexane and isopropanol
  5. customdried
  6. customUpon drying

Sources & evidence

ORD record
ord-852ccd5ecccd420cb879adc1a6e7f2c2
Source dataset
uspto-grants-1983_11
Patent number
US04413009

Reaction notes

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