Thionyl Chloride → HCID 13772039, compound

HRID 980893Notes

Reaction equation

HRID 980893 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:19])[N:6]([CH2:16][CH2:17]O)[C:7](=[O:15])[NH:8]2.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl>[Cl:22][CH2:17][CH2:16][N:6]1[C:5](=[O:19])[C:4]2[C:9](=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:3]=2[O:2][CH3:1])[NH:8][C:7]1=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 137720413-(2-Hydroxyethyl)-5,6-dimethoxyquinazoline-2,4(1H,3H)-dione

Product 1

HCID 13772039HCID 13772039, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5,6-dimethoxy-3-hydroxyethylquinazolin-2,4-dione (2.0 g, 7.51 mM) and thionyl chloride (0.76 ml, 10.45 mM) in CHCl3 (20 ml) was heated at reflux for 4 hours under nitrogen with vigorous mechanical stirring. Trituration of the solid reaction mixture followed by drying afforded crude product as an off-white solid. The crude product was recrystallized from MeOH (100 ml) and dried to afford the title compound as a white solid; 0.86; (A); mp 118°-120° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours under nitrogen with vigorous mechanical stirring
  3. customTrituration of the solid reaction mixture
  4. customby drying
  5. customafforded crude product as an off-white solid
  6. customThe crude product was recrystallized from MeOH (100 ml)
  7. customdried

Sources & evidence

ORD record
ord-0436b65a80b34eaea386ff8367df3820
Source dataset
uspto-grants-1987_01
Patent number
US04639518

Reaction notes

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