Acetic Acid → HCID 72491789, 화합물

HRID 602600노트

반응식

HRID 602600 반응식
CN(C)CCN.[Cl:7][C:8]1[S:12][C:11]([CH2:13][O:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:10][CH:9]=1.C(O)(=O)C.[C:30]([C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[NH:40][S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])(=O)[CH3:31]>CCO>[Cl:39][C:37]1[CH:36]=[CH:35][C:34]([NH:40][S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])=[C:33]([C:30](=[N:15][O:14][CH2:13][C:11]2[S:12][C:8]([Cl:7])=[CH:9][CH:10]=2)[CH3:31])[CH:38]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 67270650N-(5-chlorothiophen-2-ylmethoxy)phthalimideHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

생성물 1

HCID 72491789HCID 72491789, 화합물수율 90%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

N,N-Dimethylethylenediamine (178 μL, 1.54 mmol) was added to a solution of N-(5-chlorothiophen-2-ylmethoxy)phthalimide (220 mg, 0.75 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-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (211 mg, 0.70 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-(5-chlorothiophen-2-ylmethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 194 (280 mg, 90%), as white crystals. 1H n.m.r. (400 MHz, CDCl3) δ 11.37, br s, 1H, 7.63, d, J=8.8 Hz, 1H, 7.48, d, J=24 Hz, 1H, 7.33, dd, J=2.4 and 8.8 Hz, 1H, 6.94, d, J=3.8 Hz; 6.81, d, J=3.8 Hz; 5.24, s, 2H, 2.33, s, 3H. HRMS (M+) 445.9540. N-(5-Chlorothiophen-2-ylmethoxy)phthalimide was prepared using the procedure reported in U.S. Pat. No. 4,071,533.

후처리

  1. additionwas then added
  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-1d8f69103d7b44b7a43bc7795922e1f9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906538B2

반응 노트

불러오는 중…