5-Chloro-2-methoxybenzoyl chloride → (2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-1-(5-chloro-2-methoxyphenyl)ethanone

HRID 448020ノート

反応式

HRID 448020 の反応式
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:20]([C:19]1[CH:23]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[O:24][CH3:25])=[O:21])[CH2:3][CH2:4][CH3:5]

参加物

5

反応物 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

生成物 1

HCID 24953558(2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-1-(5-chloro-2-methoxyphenyl)ethanone

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of Example 1A (780 mg, 2.5 mmol) and 5-chloro-2-methoxy-benzoyl chloride (515 mg, 2.5 mmol) in CH2Cl2 (25 mL) under N2 atmosphere at 0° C. was added 4-dimethylaminopyridine (DMAP) (1.22 g. 10 mmol) and the mixture was allowed to warm to room temperature. The mixture was stirred for 20 hours, washed sequentially with saturated sodium bicarbonate and brine. The methylene chloride solution was dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was purified by chromatography over silica gel (hexane-EtOAc 1:1 as eluent) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (t, J=7 Hz, 3H), 1.39 (sextet, J=7 Hz, 2H), 1.66 (quintet, J=7 Hz, 2H), 2.15 (s, 3H), 2.20 (s, 3H), 3.85 (s, 3H), 3.90 (t, J=7 Hz, 2H), 6.54 (s, 1H), 7.10 (d, J=9 Hz, 1H), 7.40 (dd, J=9 Hz, 3 Hz, 1H), 7.65 (d, J=3 Hz, 1H); MS (ESI) m/z 352 (M+H)+. Anal calcd for C18H22ClNO2S: C, 61.44; H, 6.30; N, 3.98. Found: C, 61.34; H, 6.17; N, 3.86.

後処理

  1. washwashed sequentially with saturated sodium bicarbonate and brine
  2. dry with materialThe methylene chloride solution was dried (anhydrous MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography over silica gel (hexane-EtOAc 1:1 as eluent)

出典と根拠

ORDレコード
ord-39388975dd1a4ee1ba4edf9bb811f258
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

反応ノート

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