Triethylamine → N-(3-Methyl-2-butenyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 974562Notes

Reaction equation

HRID 974562 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].[CH3:13][C:14](C)=[CH:15]CN.C(O)(=O)C(O)=O.[F:25][C:26]([F:39])([F:38])[C:27]1[CH:37]=[CH:36][C:30]([O:31]C2CNC2)=[CH:29][CH:28]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:13][C:14]([CH3:15])=[CH:11][CH2:12][NH:8][C:1]([N:3]1[CH2:4][CH:6]([O:31][C:30]2[CH:36]=[CH:37][C:27]([C:26]([F:25])([F:38])[F:39])=[CH:28][CH:29]=2)[CH2:7]1)=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1669212-Buten-1-amine, 3-methyl-HCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 15053427N-(3-Methyl-2-butenyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.6 g. (0.022 mole) of 1,1'-carbonyldiimidazole in 100 ml of methylene chloride was cooled in a tap water bath and while stirring under nitrogen, 1.87 g (0.022 mole) of 3-methyl-2-butenylamine was added dropwise. After stirring for 1 hr, 6.2 g (0.02 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine oxalate was added all at once followed in 0.5 hr with 5 ml of triethylamine and stirring continued for an additional 16 hr. The reaction mixture was washed with 2×50 ml of water, dried over magnesium sulfate and concentrated on a rotary evaporator to yield a semi-solid residue. Trituration with isopropyl ether and filtration yielded 7 g of crude product which was recrystallized from ethanol-water to give 5.5 g (83.8%) of white crystals, m.p. 156.5°-158° C.

Workup

  1. stirringAfter stirring for 1 hr
  2. stirringstirring
  3. washThe reaction mixture was washed with 2×50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customto yield a semi-solid residue
  7. filtrationTrituration with isopropyl ether and filtration
  8. customyielded 7 g of crude product which
  9. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-fe29ebebc93741e390c925f601b150df
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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