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

HRID 602620노트

반응식

HRID 602620 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]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=O)[CH:3]=1.Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][NH2:33])=[CH:28][CH:27]=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:33][O:32][C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 67270465N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 72491672N-{4-chloro-2-[(4-fluorophenoxyimino)cyclohexylmethyl]phenyl}trifluoromethanesulfonamide수율 38%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(4-chloro-2-cyclohexanecarbonylphenyl)trifluoromethanesulfonamide 29E (410 mg, 1.11 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (200 mg, 1.22 mmol) and anhydrous NaOAc (100 mg, 1.22 mmol) in EtOH (20 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7 to CH2Cl2) to afford N-{4-chloro-2-[(4-fluorophenoxyimino)cyclohexylmethyl]phenyl}trifluoromethanesulfonamide 169 (200 mg, 38%), as a white solid. 1H n.m.r. (200 MHz, CDCl3) δ 7.54, d, J=8.8 Hz, 1H, 7.43, dd, J=2.2 and 8.8 Hz, 1H; 7.24, d, J=2.2 Hz, 1H, 7.12-6.95, m, 5H, 2.56, m, 1H, 2.14, m, 1H, 1.93-1.65, m, 5H, 1.29, m, 4H.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 3:7 to CH2Cl2)

출처 및 근거

ORD 기록
ord-3e2c51e0445a406ab6176dda9dcecb21
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

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