Acetyl chloride → N-Formyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide

HRID 2164529Notes

Reaction equation

HRID 2164529 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11]([NH2:13])=[O:12])[CH2:8]1.[C:19](OC=O)(=[O:21])C.C([O-])=O.[Na+].C(Cl)(=O)C>CCOCC>[CH:19]([NH:13][C:11]([N:9]1[CH2:8][CH:7]([O:6][C:5]2[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=2)[CH2:10]1)=[O:12])=[O:21]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 75269Acetic-formic anhydrideHCID 146291DezinamideHCID 2723810Sodium Formate

Product 1

HCID 13476971N-Formyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.524 g (0.002 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide and 1.5 ml of formic acetic anhydride (prepared by reacting sodium formate and acetyl chloride in ether at 23°-27° C. for 5.5 hr, filtering and evaporating off the ether) was stirred at room temperature for about 54 hr. The mixture was evaporated to dryness and the residue was partitioned between 7 ml methylene chloride and 2 ml water. The methylene chloride layer was separated, dried over sodium sulfate and evaporated to dryness. The residue was triturated with ether and the mixture subjected to filtration to give a solid white filter cake weighing 0.398 g after drying. The solid was stirred with more ether for 10 minutes and the mixture filtered to give 0.350 g (61%) white powder, m.p. 117.5°-119° C.

Workup

  1. customprepared
  2. customat 23°-27° C.
  3. customfor 5.5 hr
  4. filtrationfiltering
  5. customevaporating off the ether)
  6. customThe mixture was evaporated to dryness
  7. customthe residue was partitioned between 7 ml methylene chloride and 2 ml water
  8. customThe methylene chloride layer was separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness
  11. customThe residue was triturated with ether
  12. filtrationthe mixture subjected to filtration
  13. customto give a solid white filter cake
  14. customafter drying
  15. stirringThe solid was stirred with more ether for 10 minutes
  16. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-5555b1059e1a4b9a9cf1b9d706cc933c
Source dataset
uspto-grants-1985_03
Patent number
US04505907

Reaction notes

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