p-(Trifluoromethoxy)phenyl isocyanate → HCID 59363501、化合物

HRID 1957928ノート

反応式

HRID 1957928 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[CH:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])=O.[NH4+].[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=2)=[O:30])[CH:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

6

反応物 3

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 2723923Ammonium formateHCID 10442704Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

生成物 1

HCID 59363501HCID 59363501、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21584252Ethanol ethylacetate溶媒

反応条件

温度
80 °C

実験手順

304 mg (1.53 mmol) of ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate are initially charged in 6 ml of ethyl acetate/ethanol (1:1), 163 mg (0.15 mmol) of palladium (10% on activated carbon) and 580 mg (9.20 mmol) of ammonium formate are added, and the mixture is stirred at 80° C. for 1 h. After cooling, the mixture is filtered through kieselguhr, the filtercake is rinsed with ethanol and the filtrate is freed from the solvent under reduced pressure. The residue is dissolved in 6 ml of THF, 374 mg (1.84 mmol) of 4-trifluoromethoxyphenyl isocyanate are added and the mixture is stirred at RT for 1 h. The reaction solution is concentrated and the residue is purified by RP-HPLC (acetonitrile/water). This gives a solid.

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered through kieselguhr
  3. washthe filtercake is rinsed with ethanol
  4. dissolutionThe residue is dissolved in 6 ml of THF
  5. stirringthe mixture is stirred at RT for 1 h
  6. concentrationThe reaction solution is concentrated
  7. customthe residue is purified by RP-HPLC (acetonitrile/water)
  8. customThis gives a solid

出典と根拠

ORDレコード
ord-e5518b05fa734e4398a821c115047757
出典データセット
uspto-grants-2013_04
特許番号
US08410090B2

反応ノート

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