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

HRID 1668558ノート

反応式

HRID 1668558 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1623f6f3c2de46b9b763c8edb8328731
出典データセット
uspto-grants-2011_08
特許番号
US07989444B2

反応ノート

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