Water → HCID 19386910, compound

HRID 1655393Notes

Reaction equation

HRID 1655393 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]3([CH2:16][NH:17][C:18](=[O:20])[CH3:19])O[CH:9]3[C:8]=2[CH:21]=1)([O-:3])=[O:2].[NH:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27].O.C(OCC)(=O)C>C(O)C.O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[C:9]([N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])[C:8]=2[CH:21]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 120252-PyrrolidoneHCID 19386997HCID 19386997, compound

Product 1

HCID 19386910HCID 19386910, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution containing 6-nitro-3-acetamidomethyl-3,4-dihydro-3,4-epoxy-2,2-dimethyl-2H-1-benzopyran (0.5 g, 1.72 mmol), 2-pyrrolidinone (0.3 g, 3.48 mmol) and Triton B (40% in ethanol, 0.1 ml) in dioxane (10 ml) was heated at 50° C. for eighteen hours. Water and ethyl acetate were added, and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/methanol (95/5), to give crude product which on triturating with diethyl ether afforded 0.14 g of 6-nitro-2,2-dimethyl-3-acetamidomethyl-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran, m.p. 205° C.

Workup

  1. customthe organic phase separated
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with dichloromethane/methanol (95/5)
  5. customto give crude product which
  6. customon triturating with diethyl ether

Sources & evidence

ORD record
ord-96c67382d0ac42988539f96515a85d93
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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