2,4-Dichlorobenzoyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-(2,4-dichlorophenyl)ethanone

HRID 448071노트

반응식

HRID 448071 반응식
[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:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>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:17]([C:16]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:15]=1[Cl:14])=[O:18])[CH2:3][CH2:4][CH3:5]

참가 물질

4

반응물 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

생성물 1

HCID 69187202(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-(2,4-dichlorophenyl)ethanone

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

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 2,4-dichlorobenzoyl 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 0.90 (t, 3 H) 1.30-1.40 (m, 2 H) 1.58-1.65 (m, 2 H) 2.21 (s, 3 H) 2.23 (s, 3 H) 3.94-3.99 (m, 2 H) 6.11 (s, 1 H) 7.46 (dd, 1 H) 7.52-7.57 (m, 1 H) 7.62 (d, 1 H); MS (ESI) m/z 356 (M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-e7f44c3350bc4264a2554394a817f88c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481574B2

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