Water → N-(1,1-Dimethylethyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 2081429Notes

Reaction equation

HRID 2081429 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:19]=[CH:18][C:12]([O:13][CH:14]2[CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[CH3:22][C:23]([N:26]=[C:27]=[O:28])([CH3:25])[CH3:24].C(N(CC)CC)C.O>O1CCCC1>[CH3:22][C:23]([NH:26][C:27]([N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:8]([F:7])([F:20])[F:21])=[CH:19][CH:18]=2)[CH2:17]1)=[O:28])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 19799631N-(1,1-Dimethylethyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred slurry of 6.2 g (0.02 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine oxalate in 60 ml of tetrahydrofuran was treated with 2 g (0.022 mole) of 1,1-dimethylethyl isocyanate and after 0.5 hr 5 ml of triethylamine was added. The reaction slurry quickly turned to a pale yellow solution which was stirred for 18 hr, then treated with 10 ml of water. After 20 min, the tetrahydrofuran portion was separated, dried over magnesium sulfate and concentrated on a rotary evaporator. The solid residue was recrystallized from isopropyl ether to yield 5 g (79.0%) of fine white crystals, m.p. 145°-146° C.

Workup

  1. additionwas added
  2. waitAfter 20 min
  3. customthe tetrahydrofuran portion was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe solid residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-73648e3c3cbb4fd981b4b59d6d442c62
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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