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Ethyl formate → 1-(3'-Aminophenyl)-2-formylamino-propane

HRID 614872
Notes
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Reaction equation

HRID 614872 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](OCC)=[O:13]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([NH:11][CH:12]=[O:13])[CH3:10])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 204423703-(2-Aminopropyl)aniline

Product 1

HCID 213274251-(3'-Aminophenyl)-2-formylamino-propane

Procedure

A mixture of 1-(3'-amino-phenyl)-2-amino-propane and12.5 ml of ethyl formate was boiled for ten hours, and then the reaction mixture was evaporated, leaving 1-(3'-aminophenyl)-2-(formyl-amino)-propane. 4.45 gm of this amide were dissolved in 25 ml of pyridine, 2.6 ml of chlorothioformic acid-S-ethyl ester were added to the solution at 10-20° C., and the mixture was allowed to stand for a few hours. Therefore, the reaction solution was poured into ice water, and the aqueous mixture was extracted with ether. The ethereal extract was washed five times with water and once briefly with 1/10 N hydrochloric acid, and was then evaporated, leaving as a residue 1-[3'-(ethylthiocarbonyl-amino)-phenyl]-2-(formyl-amino)-propane. The residue was added to a mixture of 75 ml of methanol and 5 ml of concentrated hydrochloric acid, and the mixture was allowed to stand for three days at room temperature. Thereafter, the resulting solution was evaporated, the residue was triturated with acetonitrile, and the crystalline product formed thereby was recrystallized from acetonitrile and a little water, yielding the hydrochloride of the formula ##STR19## which has a melting point of 185°-186° C.

Workup

  1. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-4981b306caed4b1cbf23600217f28718
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04146645

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes