Water → 2,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxide

HRID 539957ノート

反応式

HRID 539957 の反応式
[O:1]=[S:2]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5](C(=O)C)[CH2:4][CH2:3]1.[OH-].[Na+].O>C(O)C>[S:2]1(=[O:16])(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 712551431-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone

生成物 1

HCID 196081962,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxide収率 76.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone (240 g, 1.0 mol) in ethanol (1.0 L) was added sodium hydroxide (200 g, 5.0 mol) and water (700 mL). The mixture was refluxed overnight and then concentrated in vacuo. The residue was extracted by ethyl acetate (1500 mL×4). The combined organic layers were extracted by hydrochloric acid (2000 mL, 3 N). The acidic aqueous layer was washed with ethyl acetate (1500 mL×2), then basified with a saturated aqueous solution of sodium bicarbonate to pH >7, and extracted with ethyl acetate (1500 mL×4). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 151 g of 2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (yield was 76%), MS obsd. (ESI+) [(M+H)1] 198, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (dd, J=1.2, 7.6 Hz, 1 H), 7.56 (t, J=7.6 Hz, 1 H), 7.47 (t, J=7.6 Hz, 1 H), 7.42 (d, J=7.6 Hz, 1 H), 4.04 (s, 2 H), 3.32-3.30 (m, 2 H), 3.30-3.25 (m, 2 H), 2.64 (s, 1 H).

後処理

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted by ethyl acetate (1500 mL×4)
  4. extractionThe combined organic layers were extracted by hydrochloric acid (2000 mL, 3 N)
  5. washThe acidic aqueous layer was washed with ethyl acetate (1500 mL×2)
  6. extractionextracted with ethyl acetate (1500 mL×4)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-38b319814cff4deea20beb02c4253bac
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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