Acetic Acid → N-[4-chloro-2-(1-cyclopropylmethoxyiminoethyl)phenyl]trifluoromethanesulfonamide

HRID 970857노트

반응식

HRID 970857 반응식
CN(C)CCN.[CH:7]1([CH2:10][O:11][N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:9][CH2:8]1.C(O)(=O)C.[C:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[NH:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])(=O)[CH3:28]>CCO>[Cl:36][C:34]1[CH:33]=[CH:32][C:31]([NH:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])=[C:30]([C:27](=[N:12][O:11][CH2:10][CH:7]2[CH2:9][CH2:8]2)[CH3:28])[CH:35]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 14843102-(cyclopropylmethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

생성물 1

HCID 86604000N-[4-chloro-2-(1-cyclopropylmethoxyiminoethyl)phenyl]trifluoromethanesulfonamide수율 81%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(cyclopropylmethoxy)phthalimide (326 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (302 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 48 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-cyclopropylmethoxyiminoethyl)phenyl]trifluoromethanesulfonamide 187 (300 mg, 81%), as a white solid. M.p. 53-54° C. 1H n.m.r. (400 MHz, CDCl3) δ 11.84, br s, 1H; 7.65, d, J=8.8 Hz, 1H; 7.49, d, J=2.4 Hz, 1H; 7.32, dd, J=2.4 and 8.8 Hz, 1H; 4.03, d, J=7.2 Hz, 2H; 2.34, s, 3H; 1.22, m, 1H; 0.64, m, 2H; 0.34, m, 2H.

후처리

  1. stirringthe mixture stirred for 48 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-26650f0db6d943278d7f6bfa0106249d
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312248B2

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