Methyl 4-chloroacetoacetate → HCID 178467470, compound

HRID 1380846Notes

Reaction equation

HRID 1380846 reaction equation
Cl.[CH2:2]([O:4][C:5](=[NH:7])[NH2:6])[CH3:3].[Cl:8][CH2:9][C:10](=O)[CH2:11][C:12](OC)=[O:13].[Na]>CO>[CH2:2]([O:4][C:5]1[N:6]=[C:10]([CH2:9][Cl:8])[CH:11]=[C:12]([OH:13])[N:7]=1)[CH3:3]

Participants

5

Reactant 3

HCID 36240Methyl 4-chloroacetoacetateHCID 5360545SodiumHCID 122987352-Ethylisouronium chloride

Product 1

HCID 178467470HCID 178467470, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 24.9 g (0.2 mol) of O-ethylisourea hydrochloride and 21.5 g (0.14 mol) of methyl 4-chloroacetoacetate in 100 ml of methanol is treated at 0°-5° C. during 10 minutes with a solution of 7.55 g (0.33 mol) of sodium in 100 ml of methanol. The mixture is stirred at 0° C. for 2 hours and at room temperature for 18 hours and the solvent is then removed by evaporation under reduced pressure. The residue is dissolved in 300 ml of water and the solution is adjusted to a pH-value of 6. The resulting crystallline product is filtered off, washed with diethyl ether and dried at 40° C. In this manner there is obtained 2-ethoxy-4-chloromethyl-6-hydroxy-pyrimidine, m.p. 157°-159° C. By back-extracting the aqueous filtrate three times with 150 ml of chloroform each time there is obtained an additional amount of this product, m.p. 159°-161° C.

Workup

  1. customthe solvent is then removed by evaporation under reduced pressure
  2. dissolutionThe residue is dissolved in 300 ml of water
  3. filtrationThe resulting crystallline product is filtered off
  4. washwashed with diethyl ether
  5. customdried at 40° C

Sources & evidence

ORD record
ord-c922cc9b35e54dfa8bc53a909857f975
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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