Thionyl Chloride → N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

HRID 649983노트

반응식

HRID 649983 반응식
[Br:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].BrC1SC(C)=CC=1C(O)=O.S(Cl)(Cl)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[OH:34]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[OH:34][C:27]1[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:26]=1[NH:25][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[S:3][C:2]=1[Br:1])=[O:8]

참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 99421632-Amino-5-methoxyphenolHCID 111175892-Bromo-5-methylthiophene-3-carboxylic acidHCID 184222542-Bromo-5-methyl-3-thiophenecarbonyl chloride

생성물 1

HCID 10860794N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide수율 56.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 1140Toluene용매2회

실험 절차

2-Bromo-5-methyl-3-thiophenecarbonyl chloride (2.6 g), prepared in the same manner as above from 2-bromo-5-methyl-3-thiophenecarboxylic acid and thionyl chloride, was suspended in toluene (20 ml). This toluene solution was added dropwise to a solution of 2-amino-5-methoxyphenol (2.0 g) in pyridine (50 ml) at 0° C. The mixture was stirred at room temperature for 2.5 hours and the solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration, and washed with diluted hydrochloric acid and diisopropyl ether to give N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (2.1 g).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with diluted hydrochloric acid and diisopropyl ether

출처 및 근거

ORD 기록
ord-1c94d5856e89420f893e5855ffbaf56d
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271225B1

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