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

HRID 480031노트

반응식

HRID 480031 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 12324096Thiomorpholine 1,1-dioxide hydrochloride수율 36.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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 and partitioned between EtOAc and H2O. The organic layer was separated and washed sequentially with dilute HCl and saturated brine, then 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 mixture was evaporated and triturated with EtOAc to afford the subtitle compound (415 mg, 36%) as a solid. Rf 0.34 (CH2Cl2/MeOH/0.88 NH3 90/10/1, v/v). MS m/z 136 (MH+).

후처리

  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 was separated
  8. washwashed sequentially with dilute HCl and saturated brine
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. temperatureheated
  12. temperatureat reflux for 2 h
  13. customafter which time the mixture was evaporated
  14. customtriturated with EtOAc

출처 및 근거

ORD 기록
ord-f80aa89c850b441983517334936a29dc
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649620B2

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