Ethanethiol → HCID 21999459, compound

HRID 1976922Notes

Reaction equation

HRID 1976922 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].Br[C:7]([F:14])([F:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>CS(C)=O>[CH2:1]([S:3][C:7]([F:14])([F:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 21999459HCID 21999459, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Ethyl mercaptan (6.8 g, 109.7 mmol) was added dropwise to a solution of 60% sodium hydride (2.6 g, 65 mmol) in dimethyl sulfoxide (80 ml) under cooling with ice, and the mixture was stirred at room temperature for 10 minutes. A solution of ethyl bromodifluoroacetate (11.2 g, 55.2 mmol) in dimethyl sulfoxide (20 ml) was added dropwise to this solution under cooling with ice, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water to conduct extraction with ether. The solvent was distilled out of the resultant extract under reduced pressure. The resultant residue was distilled under reduced pressure to obtain the intended product (6.8 g; yield: 66.7%) as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customAfter completion of the reaction
  4. extractionextraction with ether
  5. distillationThe solvent was distilled out of the resultant
  6. extractionextract under reduced pressure
  7. distillationThe resultant residue was distilled under reduced pressure
  8. customto obtain the intended product (6.8 g; yield: 66.7%) as a colorless oil

Sources & evidence

ORD record
ord-82b7706b2af0469ca6da9e2f50d6cb27
Source dataset
uspto-grants-2001_05
Patent number
US06229049B1

Reaction notes

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