Dichloromethane → 3-[(2-Chloroethyl)amino]thiolane-1,1-dione

HRID 85713Notes

Reaction equation

HRID 85713 reaction equation
O[CH2:2][CH2:3][NH:4][CH:5]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[CH2:6]1.S(Cl)([Cl:14])=O.C1COCC1.ClCCl>ClC(Cl)C>[Cl:14][CH2:2][CH2:3][NH:4][CH:5]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[CH2:6]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 4229713-[(2-Hydroxyethyl)amino]-1lambda~6~-thiolane-1,1-dione

Product 1

HCID 49185583-[(2-Chloroethyl)amino]thiolane-1,1-dioneYield 80.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 3-((2-hydroxyethyl)amino)tetrahydrothiophene 1,1-dioxide (260 mg, 1.451 mmol) and sulfurous dichloride (863 mg, 7.25 mmol) in dichloroethane (3 mL) was heated up at 78° C. for 3 hours. The mixture was cooled to room temperature and concentrated under reduced pressure to provide the black oil. To this black oil was added THF (5 mL) and dichloromethane (5 mL), grey-white solid was observed. The solid was filtered and collected to provide the desired product as a grey solid (230 mg, 80%). LCMS: m/e 198.1 (M+H)+, 0.60 min (method 6).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto provide the black oil
  4. filtrationThe solid was filtered
  5. customcollected

Sources & evidence

ORD record
ord-64a2ffe19d1d49d093a92f23adbefdc0
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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