Triethylamine → HCID 86645772, compound

HRID 1969311Notes

Reaction equation

HRID 1969311 reaction equation
C(N([CH2:6][CH3:7])CC)C.[S:8]1[CH2:11][CH:10]([S:12][CH2:13][CH2:14][OH:15])[CH2:9]1.C[S:17](Cl)(=O)=O>ClCCl>[C:6]([O:15][CH2:14][CH2:13][S:12][CH:10]1[CH2:11][S:8][CH2:9]1)(=[S:17])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58298045HCID 58298045, compound

Product 1

HCID 86645772HCID 86645772, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (Et3N) (18 g) was added to a dichloromethane (130 ml) solution of 2-(3-thietanylthio)ethanol (21 g). A dichloromethane (30 ml) solution of methanesulfonyl chloride (MsCl) (18 g) was added dropwise to the mixture under cooling (−15 degrees centigrade), and the reaction was carried out at 0 degree centigrade for 1 hour. Coldwater was added to the reaction mixture for partition, and then the organic layer (dichloromethane solution) was added dropwise to a methanol (200 ml) solution of potassium thioacetate (AcSK) (21 g) under cooling (5 degrees centigrade), and the reaction was carried out for 10 hours. Ethyl acetate and water were added to the reaction mixture for carrying out extraction. The organic layer was washed with water and dried with magnesium sulfate. The resultant was filtered and then concentrated under reduced pressure to obtain a desired oily product (27 g).

Workup

  1. temperatureunder cooling (−15 degrees centigrade)
  2. additionColdwater was added to the reaction mixture
  3. customfor partition
  4. additionthe organic layer (dichloromethane solution) was added dropwise to a methanol (200 ml) solution of potassium thioacetate (AcSK) (21 g)
  5. temperatureunder cooling (5 degrees centigrade)
  6. waitthe reaction was carried out for 10 hours
  7. additionEthyl acetate and water were added to the reaction mixture
  8. extractionextraction
  9. washThe organic layer was washed with water
  10. dry with materialdried with magnesium sulfate
  11. filtrationThe resultant was filtered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1841f8240c23477dbd8e78bcafb0e1e7
Source dataset
uspto-grants-2013_04
Patent number
US08426551B2

Reaction notes

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