Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Bromo-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide

HRID 1258524ノート

反応式

HRID 1258524 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:18][NH:19][O:20][CH3:21].CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:19]([O:20][CH3:21])[CH3:18])=[O:6]

参加物

6

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 581374213-Bromo-5-(pentafluorosulfur)benzoic acid

生成物 1

HCID 581374643-Bromo-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide収率 76.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒2 回

実験手順

3-Bromo-5-(pentafluorosulfanyl)benzoic acid (1.35 g) was dissolved in thionyl chloride (10 ml) while stirring, and kept under reflux with exclusion of moisture for 5 h. Then the thionyl chloride was drawn off, the residue was taken up in DCM (40 ml) and the solution was admixed with N,O-dimethylhydroxylamine hydrochloride (381 mg). Subsequently Hünig's base (0.7 ml) was added and then the mixture was stirred for 2 h. Thereafter, the mixture was dried, the residue was taken up with EA and the solution was washed five times with water. The EA phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (60 g cartridge, 4:1 n-heptane/EA). 1.1 g of the title compound were obtained.

後処理

  1. temperatureunder reflux with exclusion of moisture for 5 h
  2. stirringthe mixture was stirred for 2 h
  3. customThereafter, the mixture was dried
  4. washthe solution was washed five times with water
  5. dry with materialThe EA phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

出典と根拠

ORDレコード
ord-9da0dae061a34660bdf2b7b8c442838a
出典データセット
uspto-grants-2013_06
特許番号
US08466169B2

反応ノート

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