Ethyl chloroacetate → HCID 14638252, compound

HRID 1253188Notes

Reaction equation

HRID 1253188 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[C:14]2[O:15][CH2:16][C:17](=[O:19])[NH:18][C:13]=2[N:12]=[C:11]([CH3:20])[N:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:8][C:9]1[C:14]2[O:15][CH2:16][C:17](=[O:19])[N:18]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:13]=2[N:12]=[C:11]([CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 608089HCID 608089, compound

Product 1

HCID 14638252HCID 14638252, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of 0.41 g of ethyl chloroacetate in 5 ml of methyl ethyl ketone is dropped to a mixture containing 0.6 g of 4-chloro-2-methyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one, 0.5 g of anhydrous potassium carbonate and 15 ml of methyl ethyl ketone within 15 minutes under refluxing and stirring. Then the mixture is refluxed under stirring for 8 hours, filtered as hot and washed with methyl ethyl ketone. The filtrate is evaporated to 10 ml, cooled and the unchanged starting material is filtered out. The mother liquor is evaporated, the residue is triturated with n-hexane, the solid precipitate is filtered, washed with n-hexane and dried to give 0.59 g (68%) of product, m.p.: 69°-70° C.

Workup

  1. temperatureunder refluxing
  2. temperatureThen the mixture is refluxed
  3. stirringunder stirring for 8 hours
  4. filtrationfiltered as hot and
  5. washwashed with methyl ethyl ketone
  6. customThe filtrate is evaporated to 10 ml
  7. temperaturecooled
  8. filtrationis filtered out
  9. customThe mother liquor is evaporated
  10. customthe residue is triturated with n-hexane
  11. filtrationthe solid precipitate is filtered
  12. washwashed with n-hexane
  13. customdried

Sources & evidence

ORD record
ord-ed6cd790a05f4d7dbdfd74c82b4cc3d9
Source dataset
uspto-grants-1988_05
Patent number
US04748175

Reaction notes

Loading…