Water → 2-Aminocarbonylamino-5-(4-bromophenyl)-4-chloropyrrole-3-carboxamide

HRID 1011577Notes

Reaction equation

HRID 1011577 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]([NH:12][C:13]1[NH:14][C:15]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)=[CH:16][C:17]=1[C:18]([NH2:20])=[O:19])=[O:11].O>CN(C)C=O>[NH2:9][C:10]([NH:12][C:13]1[NH:14][C:15]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)=[C:16]([Cl:1])[C:17]=1[C:18]([NH2:20])=[O:19])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 250057042-Aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide

Product 1

HCID 592858832-Aminocarbonylamino-5-(4-bromophenyl)-4-chloropyrrole-3-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (48 mg, 0.36 mmol) was added to a solution of 2-aminocarbonylamino-5-(4-bromophenyl)pyrrole-3-carboxamide (Compound No. 1-1, 97 mg, 0.30 mmol) in anhydrous N,N-dimethylformamide (2 mL), and the mixture was stirred overnight at 50° C. After cooling, water (4 mL) was added thereto, the precipitated solid was filtered off, and washed with water (5 mL). The obtained solid was dried under reduced pressure to give the target compound (54 mg) as a pale brown solid (Yield 51%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water (5 mL)
  4. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-4d0288762c754547860d5c69e09d62bf
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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