Dimethylformamide → HCID 18793823, compound

HRID 1003932Notes

Reaction equation

HRID 1003932 reaction equation
CN(C)C=O.[C:6]1(=[O:12])[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O>[C:9]1(=[O:11])[N:10]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6](=[O:12])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 18793823HCID 18793823, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (800 ml) was added to a mixture of succinimide (248 g, 2.5 mol), potassium carbonate (346 g, 2.5 mol) and ethyl 5-bromopentanoate (400 g, 1.9 mol). The mixture was heated at 110°-120° C. for 3 h before being cooled to RT. Water (2.5 L) was added and the mixture was extracted with methyl tert-butylether (4×1 L). The combined extracts were washed with water (400 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound (310 g, 71%) as a pale yellow oil.

Workup

  1. temperatureThe mixture was heated at 110°-120° C. for 3 h
  2. extractionthe mixture was extracted with methyl tert-butylether (4×1 L)
  3. washThe combined extracts were washed with water (400 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7ae2c2ed663349118d61e2fec0e6aaa1
Source dataset
uspto-grants-2000_04
Patent number
US06048841

Reaction notes

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