Ammonia → 2-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide

HRID 1011571Notes

Reaction equation

HRID 1011571 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[NH2:10][C:11]1[NH:12][C:13]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17].N.CO>O1CCCC1.O>[NH2:5][C:3]([NH:10][C:11]1[NH:12][C:13]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])=[O:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 76400Trichloroacetyl isocyanateHCID 592859782-Amino-5-(4-bromophenyl)pyrrole-3-carboxamide

Product 1

HCID 250057042-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamideYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trichloroacetyl isocyanate (60 μL, 0.50 mmol) was added dropwise to a solution of 2-amino-5-(4-bromophenyl)pyrrole-3-carboxamide (Reference compound No. 1-1, 0.17 g, 0.60 mmol) in anhydrous tetrahydrofuran (3.0 mL) at −40° C. and the mixture was stirred for 1 hour. Furthermore, ammonia solution 2.0 M in methanol (3.0 mL, 6.0 mmol) was added thereto, and the whole was stirred at room temperature for 3 days. Water (20 mL) was added to the reaction solution, then the precipitated solid was filtered off. The obtained solid was dried under reduced pressure to give the target compound (0.070 g) as a brown solid (Yield 36%).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-1c7be30331e74cf3ab4d22d2ee4f973f
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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