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

HRID 229620

반응식

HRID 229620 반응식
[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>[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:11])[F:12])=[CH:5][C:3]=1[NH:4][C:20](=[O:21])[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-58ad7d3a43db4d45bc48ee73e169a82c
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563791B2

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