1,4-Dioxane → HCID 178490692, compound

HRID 2196803Notes

Reaction equation

HRID 2196803 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[N:4][CH:3]=1.Cl[CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1.CC(C)([O-])C.[K+].O1CCOCC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([CH:14]=1)[C:8](/[N:7]=[C:5]1\[S:6][C:2]([Cl:1])=[CH:3][N:4]\1[CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1)=[O:18]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 23665647Potassium tert-butoxideHCID 866189125-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

Product 1

HCID 178490692HCID 178490692, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 16A (1001 mg, 3.33 mmol), commercially available 4-(chloromethyl)thiazole (574 mg, 3.33 mmol), potassium t-butoxide (354 mg, 3.33 mmol) and tetrabutylammonium iodide (492 mg, 1.33 mmol) in anhydrous toluene (30 mL)/dioxane (10 mL) was refluxed for 15 h. The mixture was then cooled to room temperature, washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified using an Analogix® Intelliflash280™ (SiO2, 0-70% ethyl acetate in hexanes) to afford the title compound. 800 mg, 60% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.79 (s, 3 H), 5.54 (s, 2 H), 7.13 (d, J=8.7 Hz, 1 H), 7.49 (dd, J=8.7, 2.8 Hz, 1 H), 7.70 (dd, J=16.3, 2.4 Hz, 2 H), 7.91 (s, 1 H), 9.10 (d, J=2.0 Hz, 1 H). MS (DCI) m/z 401 (M+H)+; Anal. Calculated for C15H11Cl2N3O2S2: C, 45.01; H, 2.77; N, 10.50. Found: C, 44.83; H, 2.71; N, 10.16.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-3c818051002e4c5dab1ee9ea80ab9a51
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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