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 1181190ノート

反応式

HRID 1181190 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e9e7032d862e4bd3932ea3db3420c39b
出典データセット
uspto-grants-2007_10
特許番号
US07285553B2

反応ノート

読み込み中…