Ethyl chloroformate → HCID 15572311, compound

HRID 2286592Notes

Reaction equation

HRID 2286592 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([S:20][C:21]([F:24])([F:23])[F:22])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:35]([O:34][C:32]([N:11]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:9]=[C:10]1[S:20][C:21]([F:23])([F:22])[F:24])=[O:33])[CH3:36]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 15572247HCID 15572247, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15572311HCID 15572311, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 700 mg. (2 mmoles) of 4,5-bis(4-fluorophenyl)-2-(trifluoromethylthio)pyrrole and 330 mg. (3 mmoles) of potassium tert-butoxide in 20 ml. of toluene was heated to reflux with stirring and then cooled to room temperature under nitrogen. A solution of 700 mg. (6 mmoles) of ethyl chloroformate in 15 ml. of toluene was then added dropwise and the reaction mixture stirred at room temperature for several hours. The mixture was poured onto an aqueous sodium bicarbonate solution and the product extracted into methylene chloride. The combined organic layers were dried and concentrated to give 800 mg. of a viscous oil. The oil was purified by chromatography on Silic AR CC-7 (eluted by hexane and then by mixtures of hexane/toluene), followed by recrystallization from ethanol/water to give 400 mg. of product as colorless crystals, m.p. 54°-54.5° C.

Workup

  1. additionA mixture of 700 mg
  2. temperatureto reflux
  3. stirringthe reaction mixture stirred at room temperature for several hours
  4. extractionthe product extracted into methylene chloride
  5. customThe combined organic layers were dried
  6. concentrationconcentrated
  7. customto give 800 mg
  8. customThe oil was purified by chromatography on Silic AR CC-7 (
  9. washeluted by hexane
  10. customby mixtures of hexane/toluene), followed by recrystallization from ethanol/water
  11. customto give 400 mg

Sources & evidence

ORD record
ord-10e12214f6e147fb805381c0adbd254c
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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