Sodium Acetate → N-{4-chloro-2-[1-(4-fluorophenoxyimino)propyl]phenyl}trifluoromethanesulfonamide

HRID 970862노트

반응식

HRID 970862 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16](=O)[CH2:17][CH3:18])[CH:3]=1.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][NH2:29])=[CH:24][CH:23]=1.CC([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16](=[N:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:17][CH3:18])[CH:3]=1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 86604002N-{4-chloro-2-[1-(4-fluorophenoxyimino)propyl]phenyl}trifluoromethanesulfonamide수율 81%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (386 mg, 1.22 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (200 mg, 1.22 mmol) and anhydrous NaOAc (110 mg, 1.34 mmol) in EtOH (18 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2). The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:4) to afford N-{4-chloro-2-[1-(4-fluorophenoxyimino)propyl]phenyl}trifluoromethanesulfonamide 130 (420 mg, 81%), as a pale yellow solid. M.p. 47-48° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.25, br s, 1H; 7.71, d, J=8.8 Hz, 1H; 7.58, d, J=2.4 Hz, 1H; 7.40, dd, J=2.4 and 8.8 Hz, 1H; 7.18-7.02, m, 4H; 3.02, q, J=7.6 Hz, 2H; 1.31, t, J=7.6 Hz, 3H.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2)
  3. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:4)

출처 및 근거

ORD 기록
ord-5602fc6552194d0bbc81913a8c30bc16
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312248B2

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