Imidazole → HCID 11646308, compound

HRID 2069189Notes

Reaction equation

HRID 2069189 reaction equation
F[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].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.CN1CCN(C)C1=O.O>C(O)(=O)C>[N:22]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:19])=[O:18])[C:5]3=[O:21])[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11646308HCID 11646308, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 530 mg (1.665 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 567 mg (8.325 mmol) of imidazole and 7.7 ml of dry 1,3-dimethyl-2-imidazolidinone is heated to 140° C. (oil bath temperature) for 90 minutes in a closed vial. After cooling, the dark solution is poured on 130 ml of water and the pH adjusted to ˜5 by adding 2 M acetic acid. The precipitate formed is filtered and recrystallized four times from DMSO/water, yielding 214 mg of the title compound as a red powder, m.p. >270° C.

Workup

  1. temperatureAfter cooling
  2. customThe precipitate formed
  3. filtrationis filtered
  4. customrecrystallized four times from DMSO/water

Sources & evidence

ORD record
ord-7298d52bae754493bf18ee26c615e107
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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