Triethylamine → HCID 69054127, compound

HRID 734635Notes

Reaction equation

HRID 734635 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH:9]([CH3:11])[CH3:10].[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.O>[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])[CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 57845538HCID 57845538, compound

Product 1

HCID 69054127HCID 69054127, compoundYield 119%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.260 cm3 (1.86 mmol) of triethylamine and 0.098 cm3 (0.93 mmol) of isobutyryl chloride are added, at a temperature close to 25° C., to a solution of 0.23 g (0.93 mmol) of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in 15 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 water and then extracted with twice 50 cm3 of ethyl acetate. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.35 g of 2-isobutyrylamino-4-(4-nitro-phenyl)-1H-pyrrole-3-carboxamide in the form of a green powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 15 (d, J=7.0 Hz, 6H); 2.64 (m, 1H); from 6.50 to 8.50 (very broad m, 2H); 6.79 (d, J=2.5 Hz, 1H); 7.64 (d, J=9.0 Hz, 2H); 8.19 (d, J=9.0 Hz, 2H); 10.45 (broad s, 1H); 11.65 (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. extractionextracted with twice 50 cm3 of ethyl acetate
  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-f33555a733984f2cb8938a701f180cbf
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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