Pyridine → Phenyl [2-fluoro-5-(trifluoromethyl)phenyl]carbamate

HRID 2198071

反応式

HRID 2198071 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C1COCC1>[C:23]1([O:22][C:20](=[O:21])[NH:4][C:3]2[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[CH:7]=[CH:8][C:2]=2[F:1])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 1363492-Fluoro-5-(trifluoromethyl)aniline

生成物 1

HCID 57758149Phenyl [2-fluoro-5-(trifluoromethyl)phenyl]carbamate収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-fluoro-5-(trifluoromethyl)aniline (3.00 g, 16.7 mmol) in THF (80 mL) was added pyridine (2.71 mL, 33.5 mmol), followed by phenyl chloroformate (3.15 mL, 25.1 mmol) at rt. Some solid precipitated out. The mixture was stirred at rt overnight. Water was added to the reaction and it was extracted with EtOAc. The organic solution was washed with water (2×) and dried over MgSO4 and then filtered. The filtrate was concentrated in vacuo and purified by column chromatography (10:90 to 30:70 v/v EtOAc-hexanes) to afford the title compound (3.1 g, 62%). 1H-NMR (DMSO-d6) δ 10.36 (br s, 1H), 8.15 (d, J=7.1 Hz, 1H), 7.59 to 7.47 (m, 2H), 7.46 to 7.38 (m, 2H), 7.30 to 7.20 (m, 3H); TLC Rf=0.39 (9:1 v/v hexanes-EtOAc).

後処理

  1. customSome solid precipitated out
  2. additionWater was added to the reaction and it
  3. extractionwas extracted with EtOAc
  4. washThe organic solution was washed with water (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by column chromatography (10:90 to 30:70 v/v EtOAc-hexanes)

出典と根拠

ORDレコード
ord-33b1d468d9f3417aa9cefbe9dfd27d48
出典データセット
uspto-grants-2012_12
特許番号
US08338595B2

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