Thionyl Chloride → N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

HRID 1281858노트

반응식

HRID 1281858 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[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=1[OH:33].C(OC(C)C)(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[OH:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([CH3:32])[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

8

반응물 5

HCID 24386Thionyl ChlorideHCID 30141382-Amino-m-cresolHCID 111175892-Bromo-5-methylthiophene-3-carboxylic acidHCID 184222542-Bromo-5-methyl-3-thiophenecarbonyl chlorideHCID 22281796Diisopropylether ethyl acetate

생성물 1

HCID 11110188N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide수율 84.7%

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-3-methylphenol (1.4 g) in pyridine (30 ml) at 0° C. The mixture was stirred at room temperature for 3 hours and diisopropyl ether-ethyl acetate was added. 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-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (3.0 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-22940ab0c11f4e49b705d3df759681af
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455521B1

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