1-Hydroxybenzotriazole → N-[2-(4-chlorophenoxy)ethyl]-3-(3,4-dimethoxybenzamido)-4-methylbenzamide

HRID 502033Notes

Reaction equation

HRID 502033 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:18]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:24]([OH:26])=O)=[O:19].[Cl:36][C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43][NH2:44])=[CH:39][CH:38]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:36][C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43][NH:44][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][C:29]([CH3:30])=[C:21]([NH:20][C:18](=[O:19])[C:17]3[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:15]([O:14][CH3:13])[CH:16]=3)[CH:22]=2)=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27941912-(4-Chlorophenoxy)ethylamineHCID 36001793-[(3,4-Dimethoxybenzoyl)amino]-4-methylbenzoic acid

Product 1

HCID 22636102N-[2-(4-chlorophenoxy)ethyl]-3-(3,4-dimethoxybenzamido)-4-methylbenzamideYield 67.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.095 g) in methylene chloride (5 ml) was added to a stirred mixture of 3-(3,4-dimethoxybenzamido)-4-methylbenzoic acid (0.157 g), 2-(4-chlorophenoxy)ethylamine (C. Chim. Ther., 1973, 8, 259; 0.086 g), 4-dimethylaminopyridine (0.007 g), 1-hydroxybenzotriazole (0.074 g) and methylene chloride (5 ml). The resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was washed with an aqueous citric acid solution, dried over magnesium sulphate and evaporated. There was thus obtained the title compound as a solid (0.158 g); Mass Spectrum: M+H+ 469.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. washThe organic phase was washed with an aqueous citric acid solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-d534d7fcd7fa4f299534f054646de1cd
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

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