Water → HCID 19854544, compound

HRID 1649718Notes

Reaction equation

HRID 1649718 reaction equation
[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].O>CS(C)=O>[C:26]1(=[O:35])[N:25]([CH2:24][CH2:23][CH2:22][N:4]([C:5]2[CH:18]=[CH:17][C:8]([C:9]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:7][CH:6]=2)[C:1](=[O:3])[CH3:2])[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]12

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 148935064-(4-Acetamidophenyl)-3-methyl-4-oxobutanoic acid

Product 1

HCID 19854544HCID 19854544, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

30.0 g (120 mmol) of 3-(4-acetamidobenzoyl)-butyric acid are added to a suspension of 7.6 g (253 mmol) of sodium hydride (80%) in 150 ml of dimethyl sulphoxide and the mixture is stirred for 30 minutes at 60° C. After the addition of 33.2 g (120 mmol) of N-(3-bromopropyl)-phthalimide, stirring is continued at 80° C. for 6 hours. After cooling, the reaction mixture is poured out on 200 ml of iced water and extracted with 3×100 ml of dichloromethane. The extracts are discarded. The aqueous phase is then adjusted to pH 6.5 with 2N hydrochloric acid and again extracted with 3×100 ml of dichloromethane. The combined organic phases are dried and concentrated by evaporation under vacuum. The oil obtained as residue crystallizes when triturated with 20 ml of ethanol.

Workup

  1. stirringstirring
  2. waitis continued at 80° C. for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with 3×100 ml of dichloromethane
  5. extractionagain extracted with 3×100 ml of dichloromethane
  6. customThe combined organic phases are dried
  7. concentrationconcentrated by evaporation under vacuum
  8. customThe oil obtained as residue
  9. customcrystallizes when
  10. customtriturated with 20 ml of ethanol

Sources & evidence

ORD record
ord-29bc8c2eef6748ffbafbb550c6324269
Source dataset
uspto-grants-1990_05
Patent number
US04921856

Reaction notes

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