Propyl isocyanate → HCID 19799609, compound

HRID 1886620Notes

Reaction equation

HRID 1886620 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 etherisopropyl 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-ebad93494500445e99f3348684a924b9
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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