5-Amino-2-methylphenol → 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide

HRID 2190442노트

반응식

HRID 2190442 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:14][CH2:13]1)#[N:11].C(Cl)(=O)C(Cl)=O.C(=O)([O-])O.[Na+]>O.O1CCCC1.CN(C)C=O>[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=2)=[O:19])[CH2:13][CH2:14]1)#[N:11]

참가 물질

8

반응물 4

HCID 178185-Amino-2-methylphenolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

생성물 1

HCID 673125573-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide수율 87.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Using 5-amino-2-methylphenol (6.00 g, 48.5 mmol), 3-(1-cyanocyclopropyl)benzoic acid (6.00 g, 48.5 mmol) produced in Example A1(iii), oxalyl chloride (6.40 mL, 73.0 mmol), N,N-dimethylformamide (40 μL), tetrahydrofuran (250 mL), sodium hydrogencarbonate (6.20 g, 73.0 mmol) and water (60 mL) as starting materials, and in the same manner as in Example A32(i), the title compound (12.4 g, 87%) was obtained as a white powder. The title compound was washed with a mixed solvent of ethyl acetate and hexane.

출처 및 근거

ORD 기록
ord-9d7c02803abc4c4691af04383fdd01f5
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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