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

HRID 1281858ノート

反応式

HRID 1281858 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-22940ab0c11f4e49b705d3df759681af
出典データセット
uspto-grants-2002_09
特許番号
US06455521B1

反応ノート

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