Propyl isocyanate → HCID 19799609, compound

HRID 2081423Notes

Reaction equation

HRID 2081423 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[CH2:16]([N:19]=[C:20]=[O:21])[CH2:17][CH3:18]>C1C=CC=CC=1>[CH2:16]([NH:19][C:20]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[CH2:8]1)=[O:21])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799609HCID 19799609, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and chilled (10°-15° C.) solution of 0.027 mole of 3-[3-(trifluoromethyl)phenoxy]azetidine in 100 ml of dry benzene was added dropwise 4.0 g (0.047 mole) of n-propyl isocyanate. The reaction mixture was stirred at room temperature for 30 minutes. The benzene was washed with dilute sodium bicarbonate (50 ml), water (25 ml), saturated sodium chloride (25 ml), and dried (sodium sulfate). The solution volume was reduced to 50 ml, and 30 ml of petroleum ether was added, yielding 6.5 g (81%) of product. Recrystallization from isopropyl ether-isopropyl alcohol gave 6.0 g of small white needles, m.p. 115°-117° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. washThe benzene was washed with dilute sodium bicarbonate (50 ml), water (25 ml), saturated sodium chloride (25 ml)
  3. dry with materialdried (sodium sulfate)
  4. additionwas added

Sources & evidence

ORD record
ord-d8ec2e5eeaed4f3b95a93a53a9834c1f
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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