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

HRID 970862ノート

反応式

HRID 970862 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5602fc6552194d0bbc81913a8c30bc16
出典データセット
uspto-grants-2007_12
特許番号
US07312248B2

反応ノート

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