Sodium hydride → HCID 178490687, compound

HRID 78536

Reaction equation

HRID 78536 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)=[O:8].[H-].[Na+].Cl[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]([CH3:15])=[CH:13][N:14]\1[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2195202-(Chloromethyl)furanHCID 26781445-chloro-2-methoxy-N-(5-methyl-1,3-thiazol-2-yl)benzamide

Product 1

HCID 178490687HCID 178490687, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 340A (0.15 g, 0.53 mmol) in 5 mL DMF was added sodium hydride (0.016 g, 0.67 mmol, 95%). After the solution was allowed to stir at ambient temperature for 30 min, 2-(chloromethyl)furan (0.08 g, 0.67 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.075 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.26 (d, J=1.36 Hz, 3H) 3.80 (s, 3H) 5.18 (s, 2H) 6.54 (s, 1H) 7.12 (d, J=8.81 Hz, 1H) 7.29 (d, J=1.36 Hz, 1H) 7.46 (dd, J=8.81, 2.71 Hz, 1H) 7.64 (t, J=1.70 Hz, 1H) 7.67-7.76 (m, 2H). m/z 363.0 (M+H)+.

Workup

  1. waitThe reaction was held at ambient temperature overnight
  2. customquenched with water
  3. extractionThe crude was extracted with ethyl acetate
  4. washthe organics washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5d5b07db2fc404bae3845a0aa036456
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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