Citric Acid → HCID 68868444, compound

HRID 1984839Notes

Reaction equation

HRID 1984839 reaction equation
C([O:3][C:4]([C:6]1[N:15]=[C:14](Cl)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17]C)[CH:12]=2)[N:7]=1)=[O:5])C.[CH2:19]([S-:21])[CH3:20].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.CCOC(C)=O>[CH2:19]([S:21][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:17])[CH:12]=2)[N:7]=[C:6]([C:4]([OH:3])=[O:5])[N:15]=1)[CH3:20]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 4459711Sodium ethanethiolateHCID 22668047Ethyl 4-chloro-6-methoxyquinazoline-2-carboxylate

Product 1

HCID 68868444HCID 68868444, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-chloro-6-methoxy-quinazoline-2-carboxylic acid ethyl ester (1.22 g, 4.574 mmol) in anhydrous DMF (4.0 mL) was added sodium ethanethiolate (3.07 g, 36.59 mmol) and the reaction mixture was heated at 140° C. for 3 h. Water and EtOAc was added . The pH of the aq. layer was adjusted to 6 with citric acid. The organic layer was separated and the aq. layer was extracted with EtOAc. The combined organic layer was washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to give 0.770 g of 4-ethylsulfanyl-6-hydroxy-quinazoline-2-carboxylic acid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aq. layer was extracted with EtOAc
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0002a0266f64f8b9ae2fba6036f114e
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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