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

HRID 227681Notes

Reaction equation

HRID 227681 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-b3b05ca241fa4c58bf3ba5b36dd10e83
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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