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

HRID 1258524노트

반응식

HRID 1258524 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9da0dae061a34660bdf2b7b8c442838a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466169B2

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