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

HRID 448029ノート

反応式

HRID 448029 の反応式
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=1)=[O:19])[CH2:3][CH2:4][CH3:5]

参加物

6

反応物 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

生成物 1

HCID 69324350(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-[3-(trifluoromethyl)phenyl]ethanone

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回HCID 22036561Dimethyl sulfoxide methanol溶媒

実験手順

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 3-(trifluoromethyl)benzoyl chloride (33.4 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved 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, MS and LC/MS. 1H NMR (500 MHz, DMSO-D6/D2O) δ ppm 0.91-0.98 (m, 3 H) 1.34-1.47 (m, 2 H) 1.61-1.72 (m, 2 H) 2.30-2.33 (m, 3 H) 4.07-4.16 (m, 2 H) 6.56-6.60 (m, 1 H) 6.66-6.72 (m, 1 H) 7.69 (t, 1 H) 7.80 (d, 1 H) 8.17-8.23 (m, 1 H) 8.27 (d, 1H); MS (ESI) positive ion 342 (M+H).

後処理

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-42bb2632316f40d8a7e8ae5254e6d6c3
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

反応ノート

読み込み中…