1-(2-Bromoethoxy)-2-ethoxybenzene → Tamsulosin

HRID 1063517

反応式

HRID 1063517 の反応式
[NH2:1][CH:2]([CH3:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1.Br[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH3:29]>CN(C)C=O>[CH3:29][CH2:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH2:19][CH2:18][NH:1][C@@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)[CH3:16]

参加物

4

反応物 2

HCID 70101831-(2-Bromoethoxy)-2-ethoxybenzeneHCID 131768115-(2-Aminopropyl)-2-methoxybenzenesulfonamide

生成物 1

HCID 129211Tamsulosin収率 89.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-(−2-aminopropyl]-2-methoxybenzenesulfonamide (200 g) was dissolved in dimethylformamide (950 ml) and 1-(2-Bromoethoxy)-2-ethoxybenzene (100.3 g) was added. The reaction mixture was heated to 80–85° C. for 4 hours. Dimethylformamide was then distilled off under vacuum. Water (1000 ml) was added to solid residue and the mixture was heated to 80–90° C. under stirring for 2 hours. The mixture was cooled to room temperature. Formed crystals were filtered off and were suspended in water (900 ml). Suspension was heated to 80–90° C. under stirring for 2 hours. Crystals were filtered, washed with water (200 ml) and dried to give tamsulosin base (150 g, 89.8%).

後処理

  1. temperatureThe reaction mixture was heated to 80–85° C. for 4 hours
  2. distillationDimethylformamide was then distilled off under vacuum
  3. additionWater (1000 ml) was added to solid residue
  4. temperaturethe mixture was heated to 80–90° C.
  5. customFormed crystals
  6. filtrationwere filtered off
  7. temperatureSuspension was heated to 80–90° C.
  8. stirringunder stirring for 2 hours
  9. filtrationCrystals were filtered
  10. washwashed with water (200 ml)
  11. customdried

出典と根拠

ORDレコード
ord-ae2a2355a73d4a43a76916fc8e19fdc4
出典データセット
uspto-grants-2005_11
特許番号
US06965051B2

関連ノート

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