Triethylamine → HCID 69060826, compound

HRID 734637Notes

Reaction equation

HRID 734637 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH2:9][CH2:10][CH3:11].[NH2:14][C:15]1[NH:16][CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[C:19]=1[C:20]([NH2:22])=[O:21]>O1CCCC1.C(OCC)(=O)C>[C:8]([NH:14][C:15]1[NH:16][CH:17]=[C:18]([C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)[C:19]=1[C:20]([NH2:22])=[O:21])(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 57845538HCID 57845538, compound

Product 1

HCID 69060826HCID 69060826, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.227 cm3 (1.62 mmol) of triethylamine and 0.085 cm3 (0.81 mmol) of butyryl chloride are added, at a temperature close to 25° C., to a solution of 0.20 g (0.81 mmol) of 2-amino-4-(4-nitro-phenyl)-1H-pyrrole-3-carboxamide in 25 cm3 of tetrahydrofuran. After stirring for 16 hours at this temperature, the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is stirred in 60 cm3 of ethyl acetate and then washed with three times 20 cm3 of water. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.221 g of 2-butyrylamino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in the form of a brown powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 0.94 (t, J=7.5 Hz, 3H); 1.63 (m, 2H); 2.36 (t, J=7.5 Hz, 2H); from 6.20 to 8.50 (very broad m, 2H); 6.79 (d, J=3.0 Hz, 1H); 7.64 (d, J=9.0 Hz, 2H); 8.18 (d, J=9.0 Hz, 2H); 10.3 (broad s, 1H); 11.6 (broad s, 1H).

Workup

  1. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. washwashed with three times 20 cm3 of water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-7765419bdd4541b897909190b412c2a2
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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