Sulfuric Acid → HCID 53827548, compound

HRID 1463223Notes

Reaction equation

HRID 1463223 reaction equation
S(=O)(=O)(O)O.[CH:6]([C:9]([CH3:27])([N:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][C:24]=3[C:14]=2[C:13]1=[O:26])[C:10]#[N:11])([CH3:8])[CH3:7].[OH-].[Na+].CC[O:32]CC>C(Cl)Cl.C(OCC)(=O)C>[CH:6]([C:9]([CH3:27])([N:12]1[C:16](=[O:17])[C:15]2[CH:18]=[CH:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][C:24]=3[C:14]=2[C:13]1=[O:26])[C:10]([NH2:11])=[O:32])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53975106HCID 53975106, compound

Product 1

HCID 53827548HCID 53827548, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Concentrated sulfuric acid (5.50 mL) is added slowly to a solution of 3,6-dihydro-a-isopropyl-a,6-dimethyl-1,3-dioxobenzo[1,2-b:3,4-c']dipyrrole-2(1H)-acetonitrile (5.50 g, 19.0 mmol) in methylene chloride at 10° C. Crushed ice is added. The mixture is stirred for 24 hours at ambient temperature and poured onto crushed ice, treated with 6N sodium hydroxide to pH 2, and extracted with methylene chloride. The organic layer is separated, dried (MgSO4) and concentrated in vacuo to give an orange foamy residue. Flash chromatography (silica gel, ether then ethyl acetate eluents) affords the title product as a yellow foam (1.53 g, 25.7%), mp 159°-168° C.

Workup

  1. additionCrushed ice is added
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with methylene chloride
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an orange foamy residue

Sources & evidence

ORD record
ord-42f01cc4a645483ea4a1e0cf5198304b
Source dataset
uspto-grants-1994_04
Patent number
US05300479

Reaction notes

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