Ammonia → HCID 81430592, compound

HRID 1771712Notes

Reaction equation

HRID 1771712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5](O)=[O:6].O=S(Cl)Cl.[NH3:19]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:6])[NH2:19])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 81430592HCID 81430592, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-bromo-5-methoxycarbonyl-benzoic acid (3 g, 11.6 mmol, 1 eq) was added SOCl2 (20 mL) and the reaction heated at reflux overnight. The excess SOCl2 was removed in vacuo and the residue obtained was dissolved in THF (15 mL) and added dropwise to a solution of NH3 (38% aqueous, 30 mL). The precipitate that formed was collected by filtration, washed with water and dried to give the title compound as a white solid (2.8 g, 94%).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux overnight
  3. customThe excess SOCl2 was removed in vacuo
  4. customthe residue obtained
  5. customThe precipitate that formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d8820c0f221b4cf49ec566a59d595dc0
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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