Dichloromethane → Dezinamide

HRID 1981847Notes

Reaction equation

HRID 1981847 reaction equation
[N+]([NH:4][C:5]([NH2:7])=[O:6])([O-])=O.[F:8][C:9]([F:22])([F:21])[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH:14]1[CH2:17]N[CH2:15]1.C(Cl)Cl>C(O)C>[F:8][C:9]([F:21])([F:22])[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH:14]1[CH2:17][N:4]([C:5]([NH2:7])=[O:6])[CH2:15]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 62372NitroureaHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 146291Dezinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6 fold molar excess nitrourea and 3-[3-(trifluoromethyl)phenoxy]azetidine in a 50-50 vol. % mixture of methylene chloride and absolute ethyl alcohol is stirred at room temperature for 48 hr. The mixture is filtered. The filtrate is evaporated to dryness and the residue is partitioned between equal volumes of methylene chloride and water. The water layer is extracted 3 times with methylene chloride. The methylene chloride extracts are combined and evaporated to dryness. The residue is washed with a mixture of 1 vol. of methylene chloride to 20 volumes of toluene and filtered. The precipitate is recrystallized from ethanol/water to give pale yellow crystals. The crystals are triturated with a mixture of 2 volumes methylene chloride to 20 volumes of toluene for 2 hr. White crystals of title compound are obtained, m.p. 151°-152° C.

Workup

  1. filtrationThe mixture is filtered
  2. customThe filtrate is evaporated to dryness
  3. customthe residue is partitioned between equal volumes of methylene chloride and water
  4. extractionThe water layer is extracted 3 times with methylene chloride
  5. customevaporated to dryness
  6. washThe residue is washed with a mixture of 1 vol. of methylene chloride to 20 volumes of toluene
  7. filtrationfiltered
  8. customThe precipitate is recrystallized from ethanol/water
  9. customto give pale yellow crystals
  10. customThe crystals are triturated with a mixture of 2 volumes methylene chloride to 20 volumes of toluene for 2 hr

Sources & evidence

ORD record
ord-72730a3f5a6f49fc82fbda59dacd1cbb
Source dataset
uspto-grants-1986_06
Patent number
US04594189

Reaction notes

Loading…