Sodium Acetate → HCID 12150203, compound

HRID 1884384Notes

Reaction equation

HRID 1884384 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:24][CH2:23][O:22][C:8]=3[CH:9]=2)[N:4]=1.[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>CN(C=O)C>[C:25]([O:28][CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:24][CH2:23][O:22][C:8]=3[CH:9]=2)[N:4]=1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 12150202HCID 12150202, compound

Product 1

HCID 12150203HCID 12150203, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxy-phenyl)quinazoline (159 mg, 0.5 mmol) in DMF (2 mL) was treated with sodium acetate (104 mg, 1.2 mmol). The mixture was heated at 100° C. for 2 h, than it was poured into ice-water. The precipitated solid was collected by filtration, washed with water, and dried. The crude product was crystallized from EtOAc-hexane to give the title compound as colorless needles (95 mg); mp 144-147° C.; 1H NMR (CDCl3) 7.37 (s 1H), 7.33 (s, 1H), 7.19-7.24 (m, 2H), 6.97 (d, J=8.5, 1H), 6.15 (s, 2H), 6.07 (s, 2H), 5.41 (s, 2H), 2.24 (s, 3H). Anal. calcd. for C19H14N2O6: C, 62.30; H, 3.85; N, 7.65. Found: C, 62.12; H, 3.92; N, 7.65.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. customThe crude product was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-b3a096f8e8d74e95ac70a871e2ee3b20
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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