Pyridine → Phenyl 3-fluoro-4-(2-(methylsulfonyl)ethyl)phenylcarbamate

HRID 1843031ノート

反応式

HRID 1843031 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[NH2:5].N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>CC(C)=O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12]

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721743-Fluoro-4-(2-(methylsulfonyl)ethyl)aniline

生成物 1

HCID 86672175Phenyl 3-fluoro-4-(2-(methylsulfonyl)ethyl)phenylcarbamate収率 84%

試薬・触媒・溶媒 1

HCID 18184436N,N-dimethylformamide acetone溶媒

実験手順

To a stirred solution of 3-fluoro-4-(2-(methylsulfonyl)ethyl)aniline (200 mg, 0.92 mmol) in acetone/DMF (3 mL+1.27 mL), pyridine (0.222 mL, 2.76 mmol) was added dropwise phenyl chloroformate (0.152 mL, 1.197 mmol) at 0° C. and the mixture was stirred at room temperature for 1 h. The acetone was evaporated and the residue was diluted with DCM (30 mL). The mixture was washed with saturated NaHCO3 solution (15 mL) and the organic layer extracted with DCM (2×20 mL). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to give pure phenyl 3-fluoro-4-(2-(methylsulfonyl)ethyl)phenylcarbamate (260 mg, 84%).

後処理

  1. customThe acetone was evaporated
  2. additionthe residue was diluted with DCM (30 mL)
  3. washThe mixture was washed with saturated NaHCO3 solution (15 mL)
  4. extractionthe organic layer extracted with DCM (2×20 mL)
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-018a0e70738f44b0b7254abc26987a11
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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