Triethylamine → 2,6-DIMETHOXYBENZAMIDE

HRID 477479Notes

Reaction equation

HRID 477479 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](O)=[O:6].C([N:16](CC)CC)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([NH2:16])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151092,6-Dimethoxybenzoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 890782,6-DIMETHOXYBENZAMIDEYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 of 2,6-dimethoxybenzoic acid suspended in 200 ml of anhydrous methylene chloride are added with 7.65 ml of triethylamine and then with 3.6 ml of oxalyl chloride. The mixture after being stirred at room temperature for three hours is concentrated under reduced pressure, cooled with ice, added with 10 ml of concentrated ammonia, then stirred for half an hour, then again evaporated under reduced pressure, taken with water and filtered. The solid so obtained, after crystallization from methanol, gives 2,6-dimethoxybenzamide with melting point 208°-209° C.; yield is 54%.

Workup

  1. concentrationis concentrated under reduced pressure
  2. temperaturecooled with ice
  3. additionadded with 10 ml of concentrated ammonia
  4. stirringstirred for half an hour
  5. customagain evaporated under reduced pressure
  6. filtrationfiltered
  7. customThe solid so obtained
  8. customafter crystallization from methanol

Sources & evidence

ORD record
ord-aa8cc7d5d2714bc587a20da47d29524f
Source dataset
uspto-grants-1989_12
Patent number
US04888283

Reaction notes

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