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

HRID 5823

반응식

HRID 5823 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac2c06d7cbfb4525b6d01a68903c4d4b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246929

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