Dimethylformamide → HCID 13175316, compound

HRID 2418216Notes

Reaction equation

HRID 2418216 reaction equation
CN(C)C=O.Cl[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O:12]=[C:13]1[N:18]2[C:19]3[C:24]([NH:25][CH2:26][C:17]2=[N:16][CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=[CH:21][CH:20]=3>O>[O:12]=[C:13]1[N:18]2[C:19]3[C:24]([N:25]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:26][C:17]2=[N:16][CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=[CH:21][CH:20]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 13175315HCID 13175315, compound

Product 1

HCID 13175316HCID 13175316, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 ml of dry dimethylformamide were saturated with nitrogen for 10 minutes before 150 mg of ethyl chloroformate and 280 mg of ethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate were added thereto. The solution obtained was left at room temperature overnight and then was poured into water. The mixture was extracted with ethyl acetate and the organic phase was dried over MgSO4 and evaporated to dryness. The residue was chromatographed over silica gel and eluted with ethyl acetate to obtain 140 mg (41% yield) of diethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2,6-dicarboxylate melting at 140°-2° C.

Workup

  1. additionwere added
  2. customThe solution obtained
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-a24dfdf9a5314ed18eb735361453d567
Source dataset
uspto-grants-1984_09
Patent number
US04472401

Reaction notes

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