Triethylamine → 3-chloro-N,N-dimethyl-4-methylamino-benzamide

HRID 1949896Notes

Reaction equation

HRID 1949896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH3:12])[C:5](O)=[O:6].C(C1NC=CN=1)([C:15]1[NH:16][CH:17]=CN=1)=O.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH3:12])[C:5]([N:16]([CH3:17])[CH3:15])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 230850783-Chloro-4-(methylamino)benzoic acid

Product 1

HCID 668685293-chloro-N,N-dimethyl-4-methylamino-benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3-chloro-4-methylamino-benzoic acid (387 mg) in dry N. N-dimethylformamide (10 mL) was added carbonyl diimidazole (440 mg). After one hour, dimethylamine. HCl (221 mg) and triethylamine (0.38 mL) were added. The reaction mixture was stirred overnight, then diluted with ethyl acetate, washed with brine, dried (MgSO4) and the solvent removed in vacuo. Purification using flash chromatography yielded 3-chloro-N,N-dimethyl-4-methylamino-benzamide.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-a235395cc8164ca7b86592449b534664
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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