Ammonia → 3-Iodobenzamide

HRID 2216879Notes

Reaction equation

HRID 2216879 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[NH3:17]>ClCCl.CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:17])=[O:6]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 120603-Iodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 2024253-IodobenzamideYield 87.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-iodobenzoic acid (4.04 g, 16.2 mmol) in dichloromethane (30 mL) was treated with 2M oxalyl chloride (16 mL, 32 mmol, hexane) followed by two drops of N,N-dimethylformamide and stirred at ambient temperature for 2 hours. After this time the solvent was removed in vacuo and the residue dissolved in tetrahydrofuran (30 ml). The solution was cooled to 0° C. and treated with 2M ammonia (20 mL, 40 mmol, methanol) and the mixture stirred for 30 minutes. The mixture was then filtered and the solvent removed in vacuo. Recrystallization of the residue from methanol afforded 3.5 g (87%) of 3-iodobenzamide, as a white solid.

Workup

  1. customAfter this time the solvent was removed in vacuo
  2. dissolutionthe residue dissolved in tetrahydrofuran (30 ml)
  3. temperatureThe solution was cooled to 0° C.
  4. stirringthe mixture stirred for 30 minutes
  5. filtrationThe mixture was then filtered
  6. customthe solvent removed in vacuo
  7. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-9096da381f63410fa568feb89b443607
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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