Hydrochloric Acid → HCID 19815166, compound

HRID 465976Notes

Reaction equation

HRID 465976 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([NH:15][O:16][CH3:17])=[O:14].[C:22]([O-])(O)=[O:23].[Na+].ClC(OCC)=O.[H-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:11]2[C:12](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13](=[O:14])[N:15]([O:16][CH3:17])[C:22]1=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 19815165HCID 19815165, compound

Product 1

HCID 19815166HCID 19815166, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(2,6-Dichloro-3-methYlphenyl)amino-N-methoxybenzamide (1.6 %) is added to a THF (20 ml) solution of NaHCO3 (0.14 g) and ethyl chloroformate (0.25 g) at -30° C. under argon. The reaction is allowed to stir overnight. The THF is evaporated and the residue is partitioned between diethyl ether and water. The organic layer is washed twice with water and brine after being dried over magnesium sulfate. The organic layer is concentrated to give a white solid, which is dissolved in THF and treated with sodium hydride at reflux for one hour under argon. The reaction is acidified with 1 N HCl and partitioned between ethyl acetate and water. The organic layer is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is adsorbed onto a silica gel pad. The pad is washed with chloroform to give the product. Recrystallization from CH2Cl2 /Et2O gives 0.64 g (52% yield) of 1-(2,6-dichloro-3-methylphenyl)-3-methoxy-2,4-(1H,3H)-quinazolinedione, mp 211°-213° C.

Workup

  1. customThe THF is evaporated
  2. customthe residue is partitioned between diethyl ether and water
  3. washThe organic layer is washed twice with water and brine
  4. dry with materialafter being dried over magnesium sulfate
  5. concentrationThe organic layer is concentrated
  6. customto give a white solid, which
  7. temperatureat reflux for one hour under argon
  8. custompartitioned between ethyl acetate and water
  9. washThe organic layer is washed with brine
  10. dry with materialdried (MgSO4)
  11. customThe solvent is evaporated
  12. washThe pad is washed with chloroform
  13. customto give the product
  14. customRecrystallization from CH2Cl2 /Et2O

Sources & evidence

ORD record
ord-2eabcf4b9aad4103a84eee4c05ecf404
Source dataset
uspto-grants-1992_10
Patent number
US05155110

Reaction notes

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