Ethyl formate → Formamide, N-[2-[3-(methylthio)phenyl]ethyl]-

HRID 2414249Notes

Reaction equation

CO[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH:12]=[O:13])[CH:6]=[CH:7][CH:8]=1.[CH3:14][S:15]C1C=C(CCN)C=CC=1.C(OC=O)C>>[CH3:14][S:15][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH:12]=[O:13])[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 8025Ethyl formate

HCID 109649013-(Methylthio)benzeneethanamine

HCID 13562936N-[2-(3-Methoxyphenyl)ethyl]formamide

Product 1

HCID 10976389Formamide, N-[2-[3-(methylthio)phenyl]ethyl]-Yield 78%

Procedure

A procedure identical to that described for the preparation of N-[2-(3-methoxy-phenyl)-ethyl]-formamide in Example 1 was followed using 2-(3-methylsulfanyl-phenyl)-ethylamine (7.4 g, 44 mmol) and formic acid ethyl ester (3.6 g, 48 mmol) to give the desired product (6.7 g, 78%). MS: 168.9 (M+1+).

Sources & evidence

ORD record: ord-c3c052edc8b5497db653696d7f076550
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812228B2

Reaction notes

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