Formic Acid → n-(3-chlorophenyl)formamide

반응식

C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][CH:5]=[O:7]

참가 물질

반응물 3

HCID 284Formic Acid

HCID 7918Acetic Anhydride

HCID 79323-Chloroaniline

생성물 1

HCID 232523n-(3-chlorophenyl)formamide수율 74%

반응 조건

온도: 60 °C

실험 절차

Acetic anhydride (189 ml, 2.0 mol) was mixed with formic acid (91 ml, 2.4 mol) at 0° C. and the mixture was stirred at 60° C. for 1 h and then cooled to 0° C. To the solution was added dropwise 3-chloroaniline (105.7 ml, 1.0 mol) and the mixture was stirred at room temperature for 18 h. After removal of solvent in vacuo, the residue was extracted with EtOAc-H2O. The organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and then concentrated. The residue was crystallized from iPr2O to give the title compound (115 g, 0.739 mol, 74%) as a colorless solid.

후처리

temperaturecooled to 0° C
stirringthe mixture was stirred at room temperature for 18 h
customAfter removal of solvent in vacuo
extractionthe residue was extracted with EtOAc-H2O
washThe organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was crystallized from iPr2O

출처 및 근거

ORD 기록: ord-9f8e65d62bcd42fc950bd3462e82b505
출처 데이터셋: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06562978B1

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