Butyl iodide → HCID 178448490, 화합물

HRID 340639노트

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HRID 340639 반응식
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.C1(C)C=CC=CC=1>[CH2:23]([N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH2:24][CH2:25][CH3:26]

참가 물질

8

반응물 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

생성물 1

HCID 178448490HCID 178448490, 화합물수율 85.3%

시약·촉매·용매 4

HCID 6225Tetraethylammonium Iodide촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

실험 절차

A mixture of Example 2C (650 mg, 2 mmol), 1-iodobutane (920 mg, 5 mmol), potassium carbonate (653 mg, 4 mmol), tetrabutylammonium iodide (20 mg, 0.05 mmol), tetrabutylammonium hydrogensulfate (20 mg, 0.06 mmol) and tetraethylammonium iodide (20 mg, 0.07 mmol) in anhydrous toluene (60 mL) was refluxed for 15 h. The mixture was then washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel (EtOAc-Hexane 1:1) to afford 650 mg of the title compound. MS (DCI/NH3) m/z 381 (M+H)+.

후처리

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed over silica gel (EtOAc-Hexane 1:1)

출처 및 근거

ORD 기록
ord-d3d60ed4735e4fb49b32cad7e2b5cd0a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895592B2

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