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

HRID 84633Notes

Reaction equation

HRID 84633 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-671406ff1a3147a4842a269222297171
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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