2-(Trifluoromethyl)benzoyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-[2-(trifluoromethyl)phenyl]ethanone

HRID 448072ノート

反応式

HRID 448072 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].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:15]([F:14])([F:25])[F:26])=[O:19])[CH2:3][CH2:4][CH3:5]

参加物

4

反応物 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

生成物 1

HCID 69187345(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-[2-(trifluoromethyl)phenyl]ethanone

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

実験手順

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by 2-(trifluoromethyl)benzoyl chloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.89 (t, 3 H) 1.27-1.37 (m, 2 H) 1.56-1.63 (m, 2 H) 2.19 (s, 3 H) 2.21 (s, 3 H) 3.90-3.96 (m, 2 H) 5.99 (s, 1 H) 7.52-7.61 (m, 2 H) 7.66-7.71 (m, 1 H) 7.72-7.77 (m, 1 H); MS (ESI) m/z 356 (M+H)+.

後処理

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-5540461840374edebd2f956427779212
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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