Hydrochloric Acid → 2-(4-fluorophenyl)-3,4-dihydro-2H-1,4-benzothiazine

HRID 1439846

反応式

HRID 1439846 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=O)[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[S:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 136907612-(4-Fluorophenyl)-2H-1,4-benzothiazin-3(4H)-one

生成物 1

HCID 189844162-(4-fluorophenyl)-3,4-dihydro-2H-1,4-benzothiazine収率 91.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (4.0 g), sodium borohydride (2.91 g) and tetrahydrofuran (100 ml) is added dropwise with stirring boron trifluoride etherate complex (12. 5 ml) at room temperature, and the mixture is refluxed for 1.5 hour. After cooling, to the mixture is added dropwise 10% hydrochloric acid (35 ml), and the mixture is further refluxed for one hour. The reaction mixture is poured into ice water and made alkaline with potassium carbonate and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and distilled to remove the solvent. The residue is recrystallized from isopropyl ether to give 2-(4-fluorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (3.45 g, yield 91%) as crystals.

後処理

  1. additionis added dropwise with stirring boron trifluoride etherate complex (12. 5 ml) at room temperature
  2. temperaturethe mixture is refluxed for 1.5 hour
  3. temperatureAfter cooling, to the mixture
  4. temperaturethe mixture is further refluxed for one hour
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer is washed
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue is recrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-488b059e0af749058875b4b319e2edcb
出典データセット
uspto-grants-1996_03
特許番号
US05496815

関連ノート

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