Allyl isocyanate → HCID 67885742, compound

HRID 1032118Notes

Reaction equation

HRID 1032118 reaction equation
[CH3:1][C@H:2]1[C@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][NH:3]1.[CH2:17]([N:20]=[C:21]=[O:22])[CH:18]=[CH2:19]>O1CCCC1.O>[CH3:1][C@H:2]1[C@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)[CH2:4][N:3]1[C:21]([NH:20][CH2:17][CH:18]=[CH2:19])=[O:22]

Participants

5

Reactant 2

HCID 15123Allyl isocyanateHCID 67885882HCID 67885882, compound

Product 1

HCID 67885742HCID 67885742, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6 g (0.015 mole) of crude trans-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine (56.6%) in 50 ml of tetrahydrofuran was treated with 1.54 g (0.0165 mole) of 2-propenyl isocyanate all at once and stirred under a blanket of nitrogen for 16 hr. The reaction mixture was diluted with water until an oil separated. The oil failed to crystallize and after 7 weeks it was triturated with isopropyl ether (3×25 ml). The combined triturates gave 400 mg of white granular crystals (8.5%), m.p. 55°-57° C.

Workup

  1. customseparated
  2. customto crystallize and after 7 weeks it
  3. customwas triturated with isopropyl ether (3×25 ml)

Sources & evidence

ORD record
ord-ac13800bdd6446b3b8be5c05e201c2d5
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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