Acetic Acid → HCID 11516556, compound

HRID 2069192Notes

Reaction equation

HRID 2069192 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[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(O)(=O)C>O>[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])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11516556HCID 11516556, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 100 mg (0.314 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide and 0.274 ml (3.14 mmol) of morpholine is heated at 140° C. (oil bath temperature) for 1 hour in a closed vial. After cooling, the residue is dissolved in water, the solution acidified with 2 M acetic acid to pH ˜5 and allowed to stand at room temperature. An orange precipitate forms which is filtered and recrystallized from DMSO/water yielding 81 mg of the title compound as an orange powder, m.p. >260° C.

Workup

  1. temperatureAfter cooling
  2. customto stand at room temperature
  3. filtrationAn orange precipitate forms which is filtered
  4. customrecrystallized from DMSO/water yielding 81 mg of the title compound as an orange powder, m.p. >260° C.

Sources & evidence

ORD record
ord-a478e53ccf5742b1a6dcf3f5f87f8f6d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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