Triethylamine → 3-(2,4,4'-trichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamide

HRID 1785631Notes

Reaction equation

HRID 1785631 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH:4]([O:12][CH:13]1[CH2:16][NH:15][CH2:14]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH:4]([O:12][CH:13]1[CH2:14][N:15]([C:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:16]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 689025303-(2,4,4'-Trichlorobenzhydryloxy)azetidine

Product 1

HCID 114420773-(2,4,4'-trichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(2,4,4′-trichlorobenzhydryloxy)azetidine (4) (3 mmol) in dichloromethane (10 mL) was added tert-butyl isocyanate (3 mmol) and triethylamine (catalytic amount) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was eluted through a pre-wetted (CH2Cl2) SCX-2 (2 g) cartridge with dichloromethane to yield the desired product as a white foam (424 mg, 33%).

Workup

  1. washThe reaction mixture was eluted through a pre-wetted (CH2Cl2) SCX-2 (2 g) cartridge with dichloromethane

Sources & evidence

ORD record
ord-dadc29b445ee4248bebd3f3b717da235
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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