Sodium Acetate → N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide

HRID 602624노트

반응식

HRID 602624 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])(=O)[CH3:2].Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][NH2:31])=[CH:26][CH:25]=1.CC([O-])=O.[Na+]>CCO>[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][N:31]=[C:1]([C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:13])[F:12])=[CH:6][C:5]=2[NH:14][S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[CH3:2])=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 86604010N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 72491699N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide수율 81%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide 35 (280 mg, 0.84 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (150 mg, 0.92 mmol) and anhydrous NaOAc (75 mg, 0.92 mmol) in EtOH (15 mL) was stirred for 24 hours at RT. The reaction mixture was concentrated under vacuum, the residue purified by column chromatography (eluting with CH2Cl2/PE; 1:1 to 4:1) and the solvent removed under reduced pressure. Recrystallization from CH2Cl2/PE afforded N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide 200 (300 my, 81%), as colorless crystals. M.p. 95-96° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.48, br s, 1H, 8.01, s, 1H, 7.76, d, J=8.4 Hz, 1H, 7.55, m, 1H, 7.19-7.04, m, 4H, 2.60, s, 3H.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE; 1:1 to 4:1)
  3. customthe solvent removed under reduced pressure
  4. customRecrystallization from CH2Cl2/PE

출처 및 근거

ORD 기록
ord-f1e356611dff4e69b6c724dc7794efa9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

반응 노트

불러오는 중…