2-(Trifluoromethyl)phenyl isocyanate → tert-Butyl (2-(trifluoromethyl)phenyl)carbamate

HRID 1435919

반응식

HRID 1435919 반응식
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:12])[F:11])=[C:2]=[O:3].[CH3:14][C:15]([CH3:18])([O-:17])[CH3:16].[K+]>C1COCC1>[F:11][C:10]([F:12])([F:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:1][C:2](=[O:3])[O:17][C:15]([CH3:18])([CH3:16])[CH3:14]

참가 물질

4

반응물 2

HCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 15033883tert-Butyl (2-(trifluoromethyl)phenyl)carbamate수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-isocyanato-2-(trifluoromethyl)benzene (4.0 g, 21.4 mmol) in 50 mL of THF at 0° C. was added potassium tert-butoxide (32.0 mL of a 1M solution in THF, 32 mmol) dropwise. The reaction was allowed to stir for 3 h with warming to ambient temperature and then was quenched with 10 mL of water. The mixture was diluted with ethyl acetate and the organics were washed sequentially with 1N HCl, sat'd. aq. NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was taken up in chloroform, filtered through a pad of silica gel and concentrated to afford 2.9 g (52%) of the title compound which was sufficiently pure to be used without further purification. 1H NMR (CDCl3): δ 8.13 (d, 1H, J=8.2 Hz), 7.56 (d, 1H, J=7.7 Hz), 7.52 (t, 1H, J=8.0 Hz), 7.14 (t, 1H, J=7.7 Hz), 6.80 (broad s, 1H), 1.53 (s, 9H).

후처리

  1. customwas quenched with 10 mL of water
  2. additionThe mixture was diluted with ethyl acetate
  3. washthe organics were washed sequentially with 1N HCl
  4. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-33e2d8ed26024b4687ddf4f60985f5a7
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618980B2

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