2-Chloroethyl chloroformate → Thiomorpholine 1,1-dioxide hydrochloride

HRID 478608Notes

Reaction equation

HRID 478608 reaction equation
[Cl:1]C(OCCCl)=O.C[N:9]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[ClH:1].[NH:9]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 91413Thiomorpholine, 4-methyl-, 1,1-dioxide

Product 1

HCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideYield 36.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloroethyl chloroformate (0.72 ml, 6.7 mmol) was added dropwise to a solution of 4-methylthiomorpholine-1,1-dioxide (1.0 g, 6.7 mmol) in toluene (10 ml) at 0° C. under N2. After 10 min, the reaction was warmed and maintained at reflux for 2 h. On cooling, the reaction mixture was evaporated, partitioned between EtOAc and H2O, the organic layer separated and washed sequentially with dilute HCl and saturated brine, the organic layer dried over Na2SO4 and evaporated. The residue was taken up in MeOH (10 ml) and heated at reflux for 2 h, after which time the reaction mixture was evaporated and triturated with EtOAc to afford the subtitle compound (415 mg, 36%) as a solid. Rf 0.34 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 136 (MH+).

Workup

  1. temperaturethe reaction was warmed
  2. temperaturemaintained
  3. temperatureat reflux for 2 h
  4. temperatureOn cooling
  5. customthe reaction mixture was evaporated
  6. custompartitioned between EtOAc and H2O
  7. customthe organic layer separated
  8. washwashed sequentially with dilute HCl and saturated brine
  9. dry with materialthe organic layer dried over Na2SO4
  10. customevaporated
  11. temperatureheated
  12. temperatureat reflux for 2 h
  13. customafter which time the reaction mixture was evaporated
  14. customtriturated with EtOAc

Sources & evidence

ORD record
ord-ceea5821eff546308baaf4b4fd51d008
Source dataset
uspto-grants-2003_11
Patent number
US06642242B2

Reaction notes

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