Acetone → HCID 11107026, compound

HRID 1803048Notes

Reaction equation

HRID 1803048 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.CC(C)=O>ClCCl>[OH:4][CH2:3][CH2:2][N:1]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[CH2:5][CH2:6][OH:7]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8113DiethanolamineHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 11107026HCID 11107026, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
2.5 °C

Procedure

25 gms (0.2380 moles) of diethanolamine and 60 ml (0.4312 moles) triethylamine in 75 ml dichloromethane were taken in a reaction vessel and cooled to 0-5° C. with stirring. 40 gms (0.2554 moles) of p-methoxy benzyl chloride in 50 ml of dichloromethane was added thereto slowly. Further, the reaction mass was stirred with dichloromethane and maintained at a temperature of 25-30° C. for about 16 hours. The resulting solution was concentrated to get a residue. 200 ml of acetone was added to the residue, cooled to 0-5° C. for about one hour and filtered. The filtrate was concentrated to obtain the title compound as an oil (50.8 gms).

Workup

  1. temperaturemaintained at a temperature of 25-30° C. for about 16 hours
  2. concentrationThe resulting solution was concentrated
  3. customto get a residue
  4. temperaturecooled to 0-5° C. for about one hour
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-57c1a23d12a74f7b94a99204baee01e5
Source dataset
uspto-grants-2013_01
Patent number
US08350031B2

Reaction notes

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