Dimethylformamide → HCID 20583522, compound

HRID 411646Notes

Reaction equation

HRID 411646 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][CH:9]=[N:8][C:7]=1Cl)=[O:5])[CH3:2].[C:12]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)#[N:13].C([O-])([O-])=O.[Cs+].[Cs+].CN(C)C=O>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][CH:9]=[N:8][C:7]=1[O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:12]#[N:13])[CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 133943-CyanophenolHCID 20583525Ethyl 4-chloro-1,3-thiazole-5-carboxylate

Product 1

HCID 20583522HCID 20583522, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred of 665 mg (3.5 mmol) 4-chloro-thiazole-5-carboxylic acid ethyl ester, 416 mg (3.5 mmol) 3-cyanophenol, 2.4 g (7.3 mmol) Cs2CO3 and 60 mL dimethylformamide was warmed to 80° C. in an oil bath for 72 hours. The mixture was then cooled, poured into 70 mL water, and extracted with ethyl acetate (3×40 mL). The combined extracts were washed with water (2×50 mL), brine (1×50 mL), dried over Na2SO4, and concentrated via rotary evaporation. The resulting oil was chromatographed on a Biotage Flash 40S® silica column, loaded with methylene chloride and eluted with 20% ethyl acetate/80% hexanes to give 375 mg of a light yellow oil.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. washThe combined extracts were washed with water (2×50 mL), brine (1×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated via rotary evaporation
  6. customThe resulting oil was chromatographed on a Biotage Flash 40S® silica column
  7. washeluted with 20% ethyl acetate/80% hexanes

Sources & evidence

ORD record
ord-462fabbcc7f141e681dce87b97d617b3
Source dataset
uspto-grants-2003_05
Patent number
US06559168B2

Reaction notes

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