Water → 2-(2-Bromoethyl)-6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

HRID 1736000

반응식

HRID 1736000 반응식
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[NH:7][CH2:6][CH:5]([OH:13])[C:4]=2[CH:3]=1.[H-].[Na+].[Br:16][CH2:17][CH2:18]Br.O>CN(C=O)C>[Br:16][CH2:17][CH2:18][N:7]1[CH2:6][CH:5]([OH:13])[C:4]2[CH:3]=[C:2]([Cl:1])[S:10][C:9]=2[S:8]1(=[O:11])=[O:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 110100596-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

생성물 1

HCID 194340152-(2-Bromoethyl)-6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide (2.0 g, 8.37 mmol) in DMF (50 mL) was added sodium hydride (0.37 g, 9.2 mmol), after stirring for 30 min 1,2-dibromoethane (2.36 g, 16.7 mmol) was added and this mixture was stirred at room temperature for 72 hr. The reaction mixture was poured into water and the aqueous mixture was extracted with ether. The combined extracts were dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, 30% ethyl acetate/hexane) to give 1.52 g (53%) of the desired product as a viscous syrup which was used in the next step.

후처리

  1. additionwas added
  2. extractionthe aqueous mixture was extracted with ether
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated to an oil which
  5. customwas purified by column chromatography (silica, 30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f3251b234e1d4e36b80758ce0710c2f9
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05538966

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