Ammonia → 3-Bromo-5-methylbenzamide

HRID 564464

Reaction equation

HRID 564464 reaction equation
C1N=C[N:3](C(N2C=NC=C2)=O)C=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:17](O)=[O:18].N>CC(=O)OCC>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:17]([NH2:3])=[O:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 34331273-Bromo-5-methylbenzoic acid

Product 1

HCID 578133983-Bromo-5-methylbenzamideYield 94.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

CDI (42.2 g, 260.4 mmol) was cautiously added to a solution of 3-bromo-5-methylbenzoic acid (16.0 g, 74.4 mmol) in EA (300 mL), and then the mixture was kept at reflux for 3 h. After cooled to room temperature, NH3 (g) was passed though for 1 h. The mixture was filtered and the organic layer was washed with HCl (10%, 100 mL) and water (100 mL). The organic phase was dried over Na2SO4 and concentrated in vacuum to obtain 15.0 g of 3-bromo-5-methylbenzamide as white crystals (yield: 94%). 1H NMR (400 MHz, CDCl3): δ 7.73-7.72 (m, 1 H), 7.56-7.55 (m, 1H), 7.50-7.49 (m 1 H), 2.39 (s, 3 H).

Workup

  1. temperatureat reflux for 3 h
  2. customwas passed though for 1 h
  3. filtrationThe mixture was filtered
  4. washthe organic layer was washed with HCl (10%, 100 mL) and water (100 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-091fa4daea1343e59aa57325d8ff4317
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

Loading…