Dimethylformamide → HCID 14442113, compound

HRID 1638569Notes

Reaction equation

HRID 1638569 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16].[C:21](=O)([O-])[O-].[K+].[K+].[K+].[Br-].CN(C)[CH:31]=[O:32]>CO.[Cu]>[C:15]([C:14]1[CH:13]=[C:12]([NH:11][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([O:32][CH3:31])=[O:5])[CH:20]=[CH:19][CH:18]=1)([O:17][CH3:21])=[O:16]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 74193-Aminobenzoic AcidHCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 253877Potassium Bromide

Product 1

HCID 14442113HCID 14442113, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

To a 500 ml round-buttomed flask equipped with condenser nd N2 inlet were added 15.7 g (0.10 mol) 2-chlorobenzoic acid, 23.3 g (0.17 mol) 3-aminobenzoic acid, 23.5 g (0.17 mol) potassium carbonate, 50 mg copper powder, and 40 ml dimethylformamide. The mixture was heated to reflux, and three 50 mg portions of methanol-washed copper(I) bromide were added. The reaction was refluxed 3.5 hours, cooled, and poured into 1 1 1N HC1. The mixture was stirred for 10 minutes, filtered, and the filtered solid washed with water, methanol, and ether, and dried to afford a gray solid, mp 277°-279° C., 19 g (73.9%). The acid was taken up in 250 ml methanol, the solution saturated with HC1 and refluxed 40 hours, and cooled and evaporated. The residue was chromatographed on silica gel using methylene chloride as eluent to afford 17.46 g (61.3% overall) of a yellow oil. NMR (d, CDC13): 3.97 (s, 3H), 6.7-8.0 (m, 8H). IR (Cm.-1, KBr): 1730 (C=O).

Workup

  1. customTo a 500 ml round-buttomed flask equipped with condenser nd N2 inlet
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. washthree 50 mg portions of methanol-washed copper(I) bromide
  5. additionwere added
  6. temperatureThe reaction was refluxed 3.5 hours
  7. temperaturecooled
  8. additionpoured into 1 1 1N HC1
  9. filtrationfiltered
  10. washthe filtered solid washed with water, methanol, and ether
  11. customdried
  12. customto afford a gray solid, mp 277°-279° C., 19 g (73.9%)
  13. temperaturethe solution saturated with HC1 and refluxed 40 hours
  14. temperaturecooled
  15. customevaporated
  16. customThe residue was chromatographed on silica gel
  17. customto afford 17.46 g (61.3% overall) of a yellow oil

Sources & evidence

ORD record
ord-12700d5cc78945adb1fa3d3ca85a3402
Source dataset
uspto-grants-1989_11
Patent number
US04880810

Reaction notes

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