Sulfuric Acid → HCID 118598887, compound

HRID 1050328Notes

Reaction equation

HRID 1050328 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.Cl[C:13]1[C:32](=O)N2CCN(CC3C=CC(OC)=CC=3)C(=O)C2=C[CH:14]=1.S(=O)(=O)(O)O>O1CCOCC1>[Cl:1][C:2]1[C:7](=[O:8])[N:6]2[C:13]([CH3:32])([CH3:14])[NH:11][C:9](=[O:10])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 118598864HCID 118598864, compoundHCID 118598949HCID 118598949, compound

Product 1

HCID 118598887HCID 118598887, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-chloro-6-oxo-1,6-dihydropyridine-2-carboxamide (2, 1.4 g, 7.9 mmol) in 1,4-dioxane (20 mL), acetone (3, 4.6 g, 79 mmol) and concentrated sulfuric acid (0.038 g, 0.39 mmol) were added at room temperature and the reaction mixture was allowed to heat at 100° C. for 8 h. The reaction mixture was concentrated under reduced pressure and the residue was triturated with diethyl ether and hexane, filtered and dried to afford 6-chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (4). Yield: 1.4 g, 83%; MS (ESI) m/z 213[M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with diethyl ether and hexane
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-91cb3a30e2824632a3b42568c026f8f8
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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