p-Toluenesulfonic acid monohydrate → 3-(4-nitrophenyl)-1H-pyrrole-2-carboxamide

HRID 227681ノート

反応式

HRID 227681 の反応式
COC1C=C(OC)C=CC=1C[NH:6][C:7]([C:9]1[NH:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(#N)C>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:12]=[CH:11][NH:10][C:9]=2[C:7]([NH2:6])=[O:8])=[CH:15][CH:16]=1)([O-:22])=[O:21]

参加物

6

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 577568782-(2,4-dimethoxybenzylamino)carbonyl-3-(4-nitrophenyl)-1H-pyrrole

生成物 1

HCID 577568973-(4-nitrophenyl)-1H-pyrrole-2-carboxamide収率 42.1%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

To 1.96 g (5.139 mmol) of 2-(2,4-dimethoxybenzylamino)carbonyl-3-(4-nitrophenyl)-1H-pyrrole dissolved in 55 cm3 of toluene are added, at a temperature in the region of 20° C. under an argon atmosphere, 2.224 g (11.69 mmol) p-toluenesulfonic acid monohydrate. After stirring for 4.5 hours at a temperature in the region of 65° C., the reaction mixture is diluted with 70 cm3 of ethyl acetate and then washed successively with three times 50 cm3 of water and 50 cm3 of saturated aqueous sodium chloride solution. The resulting organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a yellow solid, which is then stirred in 15 cm3 of acetonitrile for 16 hours. After filtering through a No. 3 sinter funnel, the solid is washed with twice 4 cm3 of ice-cold acetonitrile and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 5 hours to give 0.5 g of 3-(4-nitrophenyl)-1H-pyrrole-2-carboxamide in the form of an ochre-coloured solid; EI: m/z=231: M+ base peak; m/z=214 [M−NH3]+; m/z=184 [M-HNO2]+.

後処理

  1. additionare added, at a temperature in the region of 20° C. under an argon atmosphere
  2. washwashed successively with three times 50 cm3 of water and 50 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialThe resulting organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customto give a yellow solid, which
  7. filtrationAfter filtering through a No
  8. wash3 sinter funnel, the solid is washed with twice 4 cm3 of ice-cold acetonitrile
  9. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 5 hours

出典と根拠

ORDレコード
ord-b3b05ca241fa4c58bf3ba5b36dd10e83
出典データセット
uspto-grants-2009_07
特許番号
US07560571B2

反応ノート

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