Acetic Acid → N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamide

HRID 602609노트

반응식

HRID 602609 반응식
CN(C)CCN.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][O:13][N:14]1C(=O)C2=CC=CC=C2C1=O.C(O)(=O)C.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38])=[C:32]([C:44](=O)[CH2:45][CH3:46])[CH:31]=1>CCO>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38])=[C:32]([C:44](=[N:14][O:13][CH2:12][C:8]2[S:7][CH:11]=[CH:10][CH:9]=2)[CH2:45][CH3:46])[CH:31]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 107064032-(2-Thienylmethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 86604005N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamide수율 85.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(thiophen-2-ylmethoxy)phthalimide (365 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (1 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 15 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1) to afford N-{4-chloro-2-[1-(thiophen-2-ylmethoxyimino)propyl]phenyl}trifluoromethanesulfonamide 207 (364 mg, 85%), as a white solid. M.p. 53-54° C. 1H n.m.r. (400 MHz, CDCl3) δ 11.49, br s, 1H, 7.64, d, J=8.8 Hz, 1H, 7.47, d, J=2.4 Hz, 1H, 7.33) m, 2H, 7.16, m, 1H, 7.01, m, 1H, 2.82, q, J=7.6 Hz, 2H, 1.17, t, J=7.6 Hz, 3H. HRMS (M+) 426.0065.

후처리

  1. stirringthe mixture stirred for 15 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

출처 및 근거

ORD 기록
ord-df08ee9f1b9542e6817d307ac7f5edc4
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

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