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

HRID 480031ノート

反応式

HRID 480031 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 12324096Thiomorpholine 1,1-dioxide hydrochloride収率 36.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-f80aa89c850b441983517334936a29dc
出典データセット
uspto-grants-2003_11
特許番号
US06649620B2

反応ノート

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