5-Chloro-2-(2-methoxyethoxy)-benzoyl chloride → Ethyl 2-{4-[2-(5-chloro-2-(2-methoxyethoxy)-benzamido)-ethyl]-phenyl}-propionate

HRID 1277677Notes

Reaction equation

HRID 1277677 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[C:23]([CH:27]=1)[C:24]([NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=[O:25].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[C:23]([CH:27]=1)[C:24]([NH:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:17])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)=[O:25]

Participants

4

Reactant 2

HCID 128632465-Chloro-2-(2-methoxyethoxy)-benzoyl chlorideHCID 20463406Ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride

Product 2

HCID 23453031Ethyl 2-{4-[2-(5-chloro-2-(2-methoxyethoxy)-benzamido)-ethyl]-phenyl}-propionateHCID 234530672-{4-[2-(5-Chloro-2-(2-methoxyethoxy)-benzamido)-ethyl]-phenyl}-propionic acid

Procedure

In a manner analogous to that described in Example 11, by the reaction of ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride with 5-chloro-2-(2-methoxyethoxy)-benzoyl chloride (m.p. 49°-51° C.), there is obtained, via ethyl 2-{4-[2-(5-chloro-2-(2-methoxyethoxy)-benzamido)-ethyl]-phenyl}-propionate (oil), 2-{4-[2-(5-chloro-2-(2-methoxyethoxy)-benzamido)-ethyl]-phenyl}-propionic acid; m.p. 94°-96° C., after recrystallization from isopropanol/water.

Sources & evidence

ORD record
ord-2bdadab04d1941c6852d5194a7308256
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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