Acetic Acid → 3-[(3-Chloropropyl)thio]-5-(3,4-difluorophenyl)-4-methyl-4H-1,2,4-triazole

HRID 1668558노트

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HRID 1668558 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([CH3:15])[C:11](=[S:14])[NH:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:17][CH2:18][CH2:19][Cl:20].C(O)(=O)C>C(O)C>[Cl:20][CH2:19][CH2:18][CH2:17][S:14][C:11]1[N:10]([CH3:15])[C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[N:13][N:12]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 80061-Bromo-3-chloropropaneHCID 597404455-(3,4-difluorophenyl)-4-methyl-4H-1,2,4-triazole-3-thiol

생성물 1

HCID 594655693-[(3-Chloropropyl)thio]-5-(3,4-difluorophenyl)-4-methyl-4H-1,2,4-triazole

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

To 5-(3,4-difluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.4 g, preparation reported in WO 02/40471) in ethanol (6 ml) sodium ethanolate (0.72 ml) was carefully added with stirring followed by 1-bromo-3-chloropropane (0.26 ml). The mixture was heated at 90° C. for 1 h. Acetic acid was added at room temperature until pH=4. After elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated and submitted to column chromatography (EtOAc—acetone gradient) to provide the title compound as white solid (0.36 g).

후처리

  1. customAfter elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

출처 및 근거

ORD 기록
ord-1623f6f3c2de46b9b763c8edb8328731
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989444B2

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