Potassium Carbonate → HCID 68443999, compound

HRID 2353778Notes

Reaction equation

HRID 2353778 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].I[CH2:8][CH2:9][OH:10].[ClH:11].Br[C:13]1[CH:20]=[C:19]([O:21][CH2:22][CH2:23][OH:24])[C:18]([O:25][CH3:26])=[CH:17][C:14]=1[CH2:15][NH2:16]>CN(C=O)C>[Cl:11][C:13]1[CH:20]=[C:19]([O:21][CH2:22][CH:23]([OH:24])[CH2:1][OH:4])[C:18]([O:25][CH3:26])=[CH:17][C:14]=1[CH2:15][NH:16][C:9](=[O:10])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 68441771HCID 68441771, compound

Product 1

HCID 68443999HCID 68443999, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dry K2CO3 (2 mol eq) and 2-iodoethanol (2 mol eq) were added to a solution of 2-chloro-4-hydroxy-5-methoxy-N-acetyl benzylamine 3 (0.4 g, 1.46 mmol) in dry DMF (15 ml). The mixture was refluxed for 6 hours, then the solvent was evaporated off under reduced pressure. After addition of water the aqueous layer was extracted with EtOAc (3×25 ml) and the organic phases were anhydrified over Na2SO4 and evaporated under reduced pressure to furnish the title compound as pale yellow solid (0.38 g, 81% yield).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customthe solvent was evaporated off under reduced pressure
  3. additionAfter addition of water the aqueous layer
  4. extractionwas extracted with EtOAc (3×25 ml)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-95f0f4502b5642ecade1c1f2d2aa0cd9
Source dataset
uspto-grants-2010_07
Patent number
US07750049B2

Reaction notes

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