Triethylamine → 4-Amino-3-chloro-N,N-dimethylbenzamide

HRID 1487588

Reaction equation

HRID 1487588 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].Cl.[CH3:13][N:14](C)[CH2:15]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNC>C(Cl)Cl.C(O)(C)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([CH3:15])[CH3:13])=[O:7])=[CH:4][C:3]=1[Cl:11]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 202874814-Amino-3-chloro-N,N-dimethylbenzamideYield 59.6%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3-chlorobenzoic acid (1 equiv) in DCM (0.12 M) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 equiv), 1-hydroxybenzotriazole (1.2 equiv), triethylamine (4 equiv) and dimethylamine hydrochloride (2 equiv) sequentially. The mixture was stirred at room temperature overnight. After the reaction was complete, as monitored by LCMS, the mixture was diluted with a mixture of isopropanol in chloroform (30%), washed with water and dried over anhydrous sodium sulfate. The organic phase was concentrated and the residue obtained was recrystallized in the mixture of hexane and ethyl acetate (10%) to afford the desired product (Yield: 59.6%) as a light brown solid. MS (ESI) m/z 199.1 [M+1]+.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic phase was concentrated
  4. customthe residue obtained
  5. customwas recrystallized in the mixture of hexane and ethyl acetate (10%)

Sources & evidence

ORD record
ord-d061683f71294405bc82d662ae7fa1c6
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Linked notes

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