Dimethylformamide → 2-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}-1,3-thiazole

HRID 2080387ノート

反応式

HRID 2080387 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9](O)[C:10]1[S:11][CH:12]=[CH:13][N:14]=1.CN(C)C=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>S(Cl)(Cl)=O.C(OCC)(=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23114721HCID 23114721、化合物

生成物 1

HCID 231146522-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}-1,3-thiazole収率 24%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 24386Thionyl Chloride溶媒

実験手順

The 2-[(2,5-difluorophenyl)-hydroxymethyl]thiazole (348 mg, 1.53 mmol) obtained in Referential Example 15 was dissolved in thionyl chloride (1.5 ml). To the resulting solution was added a drop of dimethylformamide. The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue, followed by further concentration under reduced pressure. The residue was dissolved in dimethylformamide (10.0 ml). To the resulting solution were added 4-chlorobenzenethiol (332 mg, 2.3 mmol) and potassium carbonate (845 mg, 6.12 mmol). The resulting mixture was stirred at 50° C. for 2 hours. After the reaction mixture was allowed to stand until it became room temperature, ethyl acetate (60 ml) was added thereto. The resulting mixture was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 6:1) to give the title compound (130 mg, 24%) as a colorless oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionDioxane was added to the residue
  3. concentrationfollowed by further concentration under reduced pressure
  4. dissolutionThe residue was dissolved in dimethylformamide (10.0 ml)
  5. stirringThe resulting mixture was stirred at 50° C. for 2 hours
  6. custombecame room temperature
  7. washThe resulting mixture was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 6:1)

出典と根拠

ORDレコード
ord-db7e6ca960c84102ae3652086b9da461
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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