Ethyl isocyanate → HCID 19799638, compound

HRID 1886618Notes

Reaction equation

HRID 1886618 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:18]=[C:19]=[O:20])[CH3:17]>C1C=CC=CC=1.C(Cl)Cl>[CH2:16]([NH:18][C:19]([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:20])[CH3:17]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799638HCID 19799638, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred and chilled (15°-20° C.) solution of 0.024 mole of 3-[3-(trifluoromethyl)phenoxy]azetidine in 50 ml of dry benzene was added dropwise 1.99 g (0.028 mole) of ethyl isocyanate. The reaction mixture was stirred at room temperature overnight and was diluted with 50 ml of methylene chloride. The solution was washed with 5% sodium hydroxide (2×50 ml), water (50 ml), saturated sodium chloride (25 ml), dried over sodium hydroxide, and concentrated in vacuo. The residue (9.6 g) was twice recrystallized from ethyl acetate-isopropyl ether to give 5.4 g of a white solid, m.p. 125°-126° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washThe solution was washed with 5% sodium hydroxide (2×50 ml), water (50 ml), saturated sodium chloride (25 ml)
  3. dry with materialdried over sodium hydroxide
  4. concentrationconcentrated in vacuo
  5. customThe residue (9.6 g) was twice recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-5c0c623927224a3b9ab75d81a99c8a7f
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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