Butyl isocyanate → HCID 19799627, compound

HRID 2081426Notes

Reaction equation

HRID 2081426 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.[CH2:16]([N:20]=[C:21]=[O:22])[CH2:17][CH2:18][CH3:19]>C(OC(C)C)(C)C>[CH2:16]([NH:20][C:21]([N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:13][CH:12]=2)[CH2:11]1)=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799627HCID 19799627, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 6.5 g (0.03 mole) of crude 3-[4-(trifluoromethyl)phenoxy]azetidine in 50 ml of isopropyl ether was stirred under a blanket of nitrogen while 4 g (0.04 mole) of n-butyl isocyanate was added dropwise. The reaction was slightly exothermic and after 30 min, a solid separated. The solid was collected by filtration after 3 hr to give 3.85 g of crystalline product, m.p. 135°-136° C. After 24 hr, a second bath of crystals was obtained; 1.5 g; m.p. 132°-134° C. The two fractions were combined and recrystallized from cyclohexane to yield 3.6 g of product (38%), m.p. 136°-137° C.

Workup

  1. additionwas added dropwise
  2. customa solid separated
  3. filtrationThe solid was collected by filtration after 3 hr

Sources & evidence

ORD record
ord-8b078dbc39cc440b8e66f71ef14e997d
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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