Synthesis of m-phenetidine

Preparation of m-phenetidine

m-Phenetidine is prepared by alkylation of 3-acetamidophenol with diethyl sulfate. Some authors suggest that better yield is obtained using ethyl bromide as the alkylating agent.

Preparation of m-phenetidine

Preparation of m-phenetidine

To the round bottom flask fitted with dropping funnel and mechanical stirrer a solution of 27 g of 3-acetamidophenol dissolved in 180 ml of potassium hydroxide is placed. The reaction mixture is gently warmed to a temperature 50-60° C, and from dropping funnel 23 ml of diethyl sulfate, added in small portions, keeping the temperature at 50-60° C. When a portion of the N-(3-ethoxyphenyl)acetamide has crystallized, the solution is treated again with one-half the initial quantities of solution of potassium hydroxide and diethyl sulfate. The reaction mixture is allowed to stand overnight and next day treated with 100 ml of concentrated aqueous ammonia in order to decompose remaining excess of diethyl sulfate. The crude N-(3-ethoxyphenyl)acetamide is filtered off, washed with a little ice-cold distilled water and boiled one-half hour with 150 ml of 15% hydrochloric acid. On cooling m-phenetidine hydrochloride crystals separates which are dissolved in water, treated with the solution of sodium hydroxide and m-phenetidine base is extracted with ether. The extract is dried over sodium sulfate and ether is removed by evaporation. The crude m-phenetidine is purified by distillation in vacuum collecting fraction boiling at 142-144° C under 20 mm pressure. The final yield of m-phenetidine is 15 g.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 34-36, 1923

IUPAC Name

3-ethoxyaniline

InChI

InChI=1S/C8H11NO/c1-2-10-8-5-3-4-7(9)6-8/h3-6H,2,9H2,1H3

InChI Key

WEZAHYDFZNTGKE-UHFFFAOYSA-N

Canonical SMILES

CCOC1=CC=CC(=C1)N

Depositor-Supplied Synonyms

m-Phenetidine, 3-ETHOXYANILINE, 621-33-0, Benzenamine, 3-ethoxy-, m-Ethoxyaniline, 3-Ethoxybenzenamine, CCRIS 4696, WEZAHYDFZNTGKE-UHFFFAOYSA-N, 3-ethoxyphenylamine, NSC 9817, EINECS 210-680-2, SBB059860, BRN 0971028, AI3-15397, 3-ethoxy aniline, NSC9817, 3-ethoxy-phenylamine, PubChem8374, PubChem9507, ACMC-1BEKT, DSSTox_CID_5862, UNII-XE9KKL972R, AC1L1YW3, AC1Q37XW, DSSTox_RID_77952, XE9KKL972R, DSSTox_GSID_25862, MLS002303035, BIDD:GT0168, SCHEMBL112380, 194492_ALDRICH, AC1Q363J, ARONIS023711, CHEMBL1466168, CTK2F6464, MolPort-000-900-819, HMS3039P08, CS-B0033, NSC-9817, Tox21_200997, ANW-66172, KM0577, ZINC00157624, AKOS000136944, LS-1486, MCULE-1211983120, RP20366, NCGC00091613-01, NCGC00091613-02, NCGC00258550-01, AJ-15085, AK-81722, AN-46703, CAS-621-33-0, KB-70750, SC-05815, SMR001307326, ZB006748, DB-054070, RT-004173, FT-0629003, ST51046123, EN300-49840, 4-13-00-00954 (Beilstein Handbook Reference), A833599, 3B3-020265, InChI=1/C8H11NO/c1-2-10-8-5-3-4-7(9)6-8/h3-6H,2,9H2,1H

Removed Synonyms

(3-ethoxyphenyl)amine, 3-METHOXYANILINE, CID12120, 536-90-3

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