Dimethylformamide → HCID 59496105, compound

HRID 1513342Notes

Reaction equation

HRID 1513342 reaction equation
[C:1]1([C:7]2[C:8](=[O:22])[N:9]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](N(CC)CC)[CH3:24].CN(C)[CH:32]=[O:33]>>[O:13]=[C:10]1[N:9]([C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[C:8](=[O:22])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:12][N:11]1[CH2:23][CH2:24][CH:32]=[O:33]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 59496108HCID 59496108, compound

Product 1

HCID 59496105HCID 59496105, compoundYield 77%

Procedure

To a solution of 6-phenyl-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (84 mg, 0.286 mmol) in N,N-Dimethylformamide (DMF) (2 ml) under an argon atmosphere, triethylamine (0.050 ml, 0.359 mmol) was added and the mixture stirred at r.t. for 5 min., then acroleyn (0.020 ml, 0.299 mmol) was added and the mixture stirred overnight. Reaction was quenched by sat. NH4Cl (4 mL) and aq. layer extracted by Et2O (2×10 mL). Combined organic layers were washed by iced water, dried upon sodium sulphate and concentrated under reduced pressure to obtain 77 mg of title (77% yield).

Workup

  1. additionacroleyn (0.020 ml, 0.299 mmol) was added
  2. stirringthe mixture stirred overnight
  3. customReaction
  4. customwas quenched by sat. NH4Cl (4 mL) and aq. layer
  5. extractionextracted by Et2O (2×10 mL)
  6. washCombined organic layers were washed by iced water
  7. dry with materialdried upon sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain 77 mg of title (77% yield)

Sources & evidence

ORD record
ord-45e0a7eaeaa84bf7a87aa8fb55f21dd8
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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