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

HRID 1435919ノート

反応式

HRID 1435919 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33e2d8ed26024b4687ddf4f60985f5a7
出典データセット
uspto-grants-2009_11
特許番号
US07618980B2

反応ノート

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