Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → N-[6-(3-Formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 2069199Notes

Reaction equation

HRID 2069199 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].C[O:23][CH:24]1[CH:28]([CH:29]=O)[CH2:27][CH:26](OC)O1>C(O)(=O)C.C(OCC)(=O)C>[CH:24]([C:28]1[CH:27]=[CH:26][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:5]3=[O:21])[CH:29]=1)=[O:23]

Participants

5

Reactant 2

HCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 11674068N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11574709N-[6-(3-Formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(6-amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (470 mg, 1.49 mmol) and 2,5-dimethoxytetrahydrofuran-3-aldehyde (796 mg, 4.47 mmol) in acetic acid (0.5 ml) is refluxed for five hours. The solvent is removed by rotavapor evaporation to give a brown oil which is dissolved in ethyl acetate and washed three times with water. The organic layer is dried over magnesium sulfate, filtered and the solvent removed by rotavapor evaporation to give the title compound nearly pure as a brown solid, m.p. 230-245° C. (decomp).

Workup

  1. customThe solvent is removed by rotavapor evaporation
  2. customto give a brown oil which
  3. washwashed three times with water
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed by rotavapor evaporation

Sources & evidence

ORD record
ord-230093f861a84476abfde61b1ac46a30
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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