1,4-Dibromobutane → 6-chloro-3,4-dihydro-2-(4-bromobutyl)-2H-thieno[3,2-e]-1,2-thiazine-4-ol 1,1-dioxide

HRID 1181190노트

반응식

HRID 1181190 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][CH2:19][CH2:20]Br>CN(C)C=O>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:11])(=[O:12])[N:7]([CH2:20][CH2:19][CH2:18][CH2:17][Br:16])[CH2:6][CH:5]([OH:13])[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 110100596-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

생성물 1

HCID 220580556-chloro-3,4-dihydro-2-(4-bromobutyl)-2H-thieno[3,2-e]-1,2-thiazine-4-ol 1,1-dioxide수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution 6-chloro-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-4-ol 1,1-dioxide (9.0 g, 37.6 mmol) in dimethylformamide (200 mL, anhydrous) and sodium hydride (60% in oil, 1.66 g, 41.5 mmol) was reacted with 1,4-dibromobutane at 0°. The reaction was stirred in an ice bath for 30 min and then it was allowed to warm to room temperature and stir for three days. The mixture was poured into ice water (400 mL) and extracted with diethyl ether (2×200 mL). The combined organic layers were washed with water (200 mL), brine (200 mL) and then were dried over magnesium sulfate and evaporated. The resulting residue was purified by silica gel flash chromatography with hexane/ethyl acetate (7:3) to give 6-chloro-3,4-dihydro-2-(4-bromobutyl)-2H-thieno[3,2-e]-1,2-thiazine-4-ol 1,1-dioxide as a colorless oil (10.62 g, 75%); the 1H NMR was consistent with the structure.

후처리

  1. stirringstir for three days
  2. extractionextracted with diethyl ether (2×200 mL)
  3. washThe combined organic layers were washed with water (200 mL), brine (200 mL)
  4. dry with materialwere dried over magnesium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel flash chromatography with hexane/ethyl acetate (7:3)

출처 및 근거

ORD 기록
ord-e9e7032d862e4bd3932ea3db3420c39b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285553B2

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