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

HRID 602608ノート

反応式

HRID 602608 の反応式
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.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[C:30]([C:42](=O)[CH2:43][CH3:44])[CH:29]=1>CCO>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[C:30]([C:42](=[N:12][O:11][CH2:10][CH:7]2[CH2:9][CH2:8]2)[CH2:43][CH3:44])[CH:29]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 14843102-(cyclopropylmethoxy)-1H-isoindole-1,3(2H)-dioneHCID 67269822N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide

生成物 1

HCID 73036091N-[4-chloro-2-(1-cyclopropylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide収率 53.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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 the addition of a solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 65 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-cyclopropylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide 196 (205 mg, 53%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.88, br s, 1H, 7.66, d, J=8.8 Hz, 1H, 7.49, d, J=2.4 Hz, 1H, 7.33, dd, J=2.4 and 8.8 Hz, 1H, 4.02, d, J=7.2 Hz, 1H, 2.83, q, J=7.6 Hz, 2H, 1.22, m, 4H, 0.64, m, 2H, 0.33, m, 2H. HRMS (M+) 384.0515. N-(cyclopropylmethoxy)phthalimide was prepared by the procedure described in Example 1G.

後処理

  1. stirringthe mixture stirred for 65 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

出典と根拠

ORDレコード
ord-e2f001c2adc04bb5bf27a4509da1460d
出典データセット
uspto-grants-2011_03
特許番号
US07906538B2

反応ノート

読み込み中…