N-methyl-2-pyrrolidone → 5-Dodecyloxy-3-(4-trifluoromethoxy-phenyl)-3H-(1,3,4)-oxadiazol-2-one

HRID 2183745Notes

Reaction equation

HRID 2183745 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:3].[F:17][C:18]([F:29])([F:28])[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1.CN1[C:35](=[O:36])CCC1>N1C=CC=CC=1>[CH2:5]([O:4][C:2]1[O:3][C:35](=[O:36])[N:26]([C:23]2[CH:22]=[CH:21][C:20]([O:19][C:18]([F:28])([F:29])[F:17])=[CH:25][CH:24]=2)[N:27]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 90513Dodecyl chloroformateHCID 605908[4-(trifluoromethoxy)phenyl]hydrazine

Product 1

HCID 102880175-Dodecyloxy-3-(4-trifluoromethoxy-phenyl)-3H-(1,3,4)-oxadiazol-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.43 mL of dodecyl chloroformate was cautiously added dropwise to a mixture consisting of 0.84 g of 4-trifluoromethoxyphenylhydrazine, 15 mL of NMP and 2 mL of pyridine while cooling in ice, and the mixture was then stirred for 2 hours while slowly warming to room temperature. After dilution with 50 mL of water, extraction by shaking was carried out with 30 mL of methylene chloride, the organic phase was dried with sodium sulfate and, while stirring and cooling in ice, 5 mL of pyridine and 3 mL of a 20% strength solution of phosgene in toluene were added dropwise. This mixture was allowed to stand overnight at room temperature and was diluted with a further 10 mL of methylene chloride and then washed 3 times with water. After drying over sodium sulfate, the mixture was concentrated in vacuo and the product was purified by column chromatography (silica gel, solvents:methanol:methylene chloride=2:98).

Workup

  1. temperaturewhile cooling in ice
  2. extractionAfter dilution with 50 mL of water, extraction
  3. stirringby shaking
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. stirringwhile stirring
  6. temperaturecooling in ice
  7. addition5 mL of pyridine and 3 mL of a 20% strength solution of phosgene in toluene were added dropwise
  8. waitto stand overnight at room temperature
  9. additionwas diluted with a further 10 mL of methylene chloride
  10. washwashed 3 times with water
  11. dry with materialAfter drying over sodium sulfate
  12. concentrationthe mixture was concentrated in vacuo
  13. customthe product was purified by column chromatography (silica gel, solvents:methanol:methylene chloride=2:98)

Sources & evidence

ORD record
ord-ecf0c422dee24fabb1e8ef6b9fb118f8
Source dataset
uspto-grants-2005_05
Patent number
US06900233B2

Reaction notes

Loading…