Sodium Acetate → N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide

HRID 602611노트

반응식

HRID 602611 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]([CH:16]=O)[CH:3]=1.Cl.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][NH2:25].CC([O-])=O.[Na+]>CCO>[F:19][C:20]([F:34])([F:35])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][N:25]=[CH:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11]

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 86230463O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochlorideHCID 86230476N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 86604006N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide 24 (180 mg, 0.63 mmol), O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride (342 mg, 1.16 mmol) and anhydrous NaOAc (141 mg, 1.72 mmol) in EtOH (10 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 CHCl3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 3:7) afforded N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide 65 (192 mg, 58%), as a yellow solid. M.p. 65-67° C. 1H n.m.r. (200 MHz, CDCl3) δ 10.38, br s, 1H, 8.20, s, 1H, 7.97, s, 1H, 7.86, d, J=8.0 Hz, 1H, 7.75, d, J=8.0 Hz, 1H; 7.65, d, J=8.8 Hz, 1H, 7.35, dd, J=2.4 and 8.8 Hz, 1H, 7.28, d, J=2.4 Hz, 1H, 5.44, s, 2H.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CHCl3)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9 to 3:7)

출처 및 근거

ORD 기록
ord-5ab1cdd27a154dd8a2578928cea44582
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

반응 노트

불러오는 중…