Sodium Hydroxide → HCID 12150188, compound

HRID 1993321Notes

Reaction equation

HRID 1993321 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:19]4[C:14](=[CH:15][C:16]5[O:22][CH2:21][O:20][C:17]=5[CH:18]=4)[NH:13][C:12](=O)[N:11]=3)=[CH:4][C:3]=2[O:2]1.P(Cl)(Cl)([Cl:26])=O.[OH-].[Na+]>CN(C=O)C>[Cl:26][C:12]1[N:11]=[C:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[C:19]2[C:14](=[CH:15][C:16]3[O:22][CH2:21][O:20][C:17]=3[CH:18]=2)[N:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 23505652HCID 23505652, compound

Product 1

HCID 12150188HCID 12150188, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

4-(3,4-Methylenedioxyphenyl)-6,7-methylenedioxyquinazolin-2(1H)-one (1 g, 3.23 mmol) was treated with DMF (one drop) and phosphorous oxychloride (7 mL, 75 mmol) and the suspension was heated to reflux for 4 h. Upon cooling to rt, the reaction mixture was poured into ice and the pH was adjusted to ˜8 with 3N NaOH solution. The precipitate was vacuum filtered and dried to give the title compound as a brown granular solid (1.18 g). 1H NMR (DMSO-d6) 6.16 (s, 2H), 6.32 (s, 2H), 6.85-7.41 (m, 5H).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 4 h
  3. additionthe reaction mixture was poured into ice
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-2ec02152d0104252846e622670a8b85c
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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