Phenethylamine → 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

HRID 1658598

Reaction equation

HRID 1658598 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15](S(N)(=O)=O)=[CH:14][CH:13]=1)=[O:8].ClC1C=C(C(O)=O)C(O)=CC=1.COC(=O)C1C=C(Cl)C=CC=1OC.C(N)CC1C=CC=CC=1>>[CH2:10]([NH:9][C:7](=[O:8])[C:6]1[CH:22]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:23][CH3:24])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 1001PhenethylamineHCID 94475-Chlorosalicylic AcidHCID 855425-chloro-2-methoxy-N-(2-(4-sulfamoylphenyl)ethyl)benzamideHCID 118574Methyl 5-chloro-2-methoxybenzoate2×

Product 1

HCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamide

Procedure

A process for preparing p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzene sulfonamide which comprises the steps of methylating 5-chlorosalicylic acid to methyl-5-chloro-2-methoxybenzoate, treating methyl-5-chloro-2-methoxybenzoate with phenethylamine to obtain N-phenethyl-5-chloro-2-methoxybenzamide, subjecting said N-phenethyl-5-chloro-2-methoxybenzamide to chlorosulfonation and aminolysis to yield p-(2-{5-chloro-2-methoxybenzamido}ethyl)-benzene sulfonamide.

Sources & evidence

ORD record
ord-93d9fbeb860f44d2955f8e87a3177b3f
Source dataset
uspto-grants-1976_06
Patent number
US03965173

Linked notes

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