Water → HCID 59463314, compound

HRID 1712939Notes

Reaction equation

HRID 1712939 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C1N=C[N:16](C(N2C=NC=C2)=O)C=1.C(=O)([O-])[O-].[NH4+].[NH4+].O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4]([NH2:16])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 517111Ammonium CarbonateHCID 532167011035235-21-2

Product 1

HCID 59463314HCID 59463314, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of give 2-bromo-5-(dimethylamino)benzoic acid (7.89 g, 32.3 mmol) in DMF (25 mL) was added N,N-carbonyldiimidazole (13.1 g, 80.8 mmol). The reaction mixture was allowed to stir at rt for 30 min and then ammonium carbonate (14.0 g, 145 mmol) was added. The reaction mixture was allowed to stir at rt overnight and then poured into water. The mixture was extracted with EtOAc. The organic solutions were combined, washed with water and brine, dried over Na2SO4, filtered and concentrated to give 2-bromo-5-(dimethylamino)benzamide (2.14 g, 27%). The product could be further purified by recrystallization from MeOH.

Workup

  1. stirringto stir at rt overnight
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d6415d867c9a449a8b59602129532374
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

Loading…