Acetic Acid → HCID 23505626, compound

HRID 1884393Notes

Reaction equation

HRID 1884393 reaction equation
C1CO[C:16]23[O:17][CH2:18][O:19][C:15]2=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[C:4]([NH2:22])[CH:3]3O1.[O-:23][C:24]#[N:25].[Na+].[OH2:27].[CH3:28][C:29]([OH:31])=O>>[CH2:18]1[O:17][C:16]2[CH:3]=[C:4]3[C:5]([C:6]([C:8]4[CH:9]=[CH:10][C:11]5[O:27][CH2:28][CH2:29][O:31][C:12]=5[CH:13]=4)=[N:25][C:24](=[O:23])[NH:22]3)=[CH:14][C:15]=2[O:19]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 517096Sodium CyanateHCID 68675897HCID 68675897, compound

Product 1

HCID 23505626HCID 23505626, compound

Procedure

3,4-(Ethylenedioxy)-2-amino-4,5-(methylenedioxy)benzophenone (15.0 g, 52.63 mmol) was dissolved in AcOH (250 mL) by heating. To this reaction mixture was added sodium cyanate (4.1 g, 63.16 mmol) and water (25 mL). The resulting mixture was then stirred at room temp. open to the air. After stirring for 18 h, excess water (120 mL) was added. The precipitate as collected by filtration. The precipitate was washed with water, and dried to give a 6,7-methylenedioxy-4-(3,4-ethylenedioxyphenyl)quinazolin-2(1H)-one as yellow solid (15.7 g); C16H10N2O5; mp>300° C. 1H NMR (DMSO) δ 11.80 (s, 1H), 7.11 (s, 1H), 7.08 (d, J=2.4 Hz, 1H), 6.98-7.02 (m, 2H), 6.79 (s, 11), 6.14 (s, 2H), 4.30 (s, 4H).

Workup

  1. temperatureby heating
  2. stirringAfter stirring for 18 h
  3. filtrationThe precipitate as collected by filtration
  4. washThe precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-8f034707a7334e689cec7a295bcb57f1
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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