Sulfuric Acid → HCID 14281515, compound

HRID 2291785Notes

Reaction equation

HRID 2291785 reaction equation
[CH:1]([C:4]([CH3:14])([N:7]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]1=[O:13])[C:5]#[N:6])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:16].[Cl-].[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH:1]([C:4]([CH3:14])([N:7]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]1=[O:13])[C:5]([NH2:6])=[O:16])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 13730721HCID 13730721, compound

Product 1

HCID 14281515HCID 14281515, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (2.0 g, 0.104 mol) in methylene chloride (30 ml) is added in a fine stream to concentrated sulfuric acid at room temperature. After stirring overnight at room temperature for 16 hours the mixture is poured onto ice, containing sodium chloride and ethyl acetate. The organic layer is washed with aqueous sodium bicarbonate, brine and dried. Evaporation after washing with ether-pentane gives a solid (72%), mp 138.5°-140° C. Anal. calcd. for C10H14N2O3 : C, 57.13; H, 6.71; N, 13.33. Found: C, 56.89; H, 6.64; N, 13.16.

Workup

  1. additionis poured onto ice
  2. washThe organic layer is washed with aqueous sodium bicarbonate, brine
  3. customdried
  4. customEvaporation
  5. washafter washing with ether-pentane

Sources & evidence

ORD record
ord-db143314de3b48128d1341f6584f5f9e
Source dataset
uspto-grants-1989_01
Patent number
US04798619

Reaction notes

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