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

HRID 974589Notes

Reaction equation

HRID 974589 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][CH:23]([N:25]=[C:26]=[O:27])[CH3:24].C(N(CC)CC)C.O>O1CCCC1>[CH3:22][CH:23]([NH:25][C:26]([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:27])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 19799636N-(1-Methylethyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 87.7%

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 1.8 g (0.022 mole) of 1-methylethyl isocyanate and after 0.5 hr, 5 ml of triethylamine was added. A clear yellow solution was obtained and was stirred for 18 hr, then treated with 10 ml of water, yielding 5.3 g (87.7%) of pale yellow crystals, m.p. 151°-152° C.

Workup

  1. customA clear yellow solution was obtained

Sources & evidence

ORD record
ord-ebbc686f4e2a4b1ca4a92dce357284ed
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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