Acetic Acid → HCID 20378262, compound

HRID 2051944Notes

Reaction equation

HRID 2051944 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].O.C(O)(=O)C>N1C=CC=CC=1>[C:12]1([C:11]2[N:10]=[C:9]([S:18][C:19]([F:23])([F:24])[CH:20]([F:22])[F:21])[N:8]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10928Ethyl chloroformate2×HCID 135080754,5-Diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole

Product 1

HCID 20378262HCID 20378262, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.76 g (5 mmole) 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole, 1.1 g (10 mmole) of ethyl chloroformate in 10 ml pyridine was stirred at RT overnight. TLC showed some starting material, so another 0.6 g (5 mmole) of ethyl chloroformate was added and stirring was continued another 24 hours. The mixture was poured into water, neutralized with acetic acid and extracted three times with ether. The ether extracts were backwashed three times with water, then dried and concentrated. The last traces of pyridine were removed by pumping at 50° (0.5 mm). The residue was chromatographed on 150 g SilicAR CC-7, eluting with toluene to give, after recrystallization from hexane, 1.05 g (55%) of white product, mp 126.5°-127°.

Workup

  1. stirringstirring
  2. waitwas continued another 24 hours
  3. extractionextracted three times with ether
  4. customdried
  5. concentrationconcentrated
  6. customThe last traces of pyridine were removed
  7. customby pumping at 50°
  8. customThe residue was chromatographed on 150 g SilicAR CC-7
  9. washeluting with toluene
  10. customto give
  11. customafter recrystallization from hexane, 1.05 g (55%) of white product, mp 126.5°-127°

Sources & evidence

ORD record
ord-27335b0aca694a54a9fede996c0499f9
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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