Dimethylformamide → HCID 68441321, compound

HRID 2353775Notes

Reaction equation

HRID 2353775 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][OH:14])[C:8]([O:15][CH3:16])=[CH:7][C:4]=1[CH2:5][NH2:6].CN([CH:20]=[O:21])C.ClC[CH:24](O)[CH2:25][OH:26]>>[Br:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]([OH:14])[CH2:20][OH:21])[C:8]([O:15][CH3:16])=[CH:7][C:4]=1[CH2:5][NH:6][C:25](=[O:26])[CH3:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 72903-Chloro-1,2-propanediolHCID 68441771HCID 68441771, compound

Product 1

HCID 68441321HCID 68441321, compoundYield 91.4%

Procedure

To a solution of 2-bromo-4-hydroxy-5-methoxy-N-acetyl benzylamine 3 (0.3 g, 1.1 mmol) in dry DMF (10 ml) dry K2CO3 (2 mol eq) and 3-chloro-1,2-dihydroxypropane (2 mol eq) were added. 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 off under reduced pressure to furnish the title compound as pale yellow solid (0.35 g, 84% 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 off under reduced pressure

Sources & evidence

ORD record
ord-f4c70805df5147fe89fedc8c4bef8200
Source dataset
uspto-grants-2010_07
Patent number
US07750049B2

Reaction notes

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