3-Ethoxy-3-oxo-2-phenylpropanoic acid → HCID 178517418, compound

HRID 2267992Notes

Reaction equation

HRID 2267992 reaction equation
[Na].Cl.[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.C([O:15][C:16](=O)[CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](O)=[O:19])C>CO>[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[N:10]=[C:18]([OH:19])[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:16]([OH:15])[N:9]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 27299033-Ethoxy-3-oxo-2-phenylpropanoic acidHCID 5360545SodiumHCID 122077144-Bromobenzene-1-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 178517418HCID 178517418, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a solution of 3.45 g (150 mmol) of sodium in 100 ml methanol, here were sequentially added 10.98 g (47 mmol) 4-bromobenzamidine hydrochloride and 11.15 g (47 mmol) of phenyl malonic acid ethyl ester. The mixture was heated for 12 hours at 80° C. The deep yellow reaction solution was filtered to remove the precipitated sodium chloride and thereafter the pyrimidine was precipitated with 10 ml of 2 molar hydrochloric acid as an intensive yellow solid. The solid was sequentially washed with water, ethanol and diethyl ether. Yield: 12.70 g (37 mmol, 79% theory) of yellow solid. The pyrimidine is insoluble in all tested organic solvents as well as in water. m.p. greater >230° C.

Workup

  1. filtrationThe deep yellow reaction solution was filtered
  2. customto remove the precipitated sodium chloride
  3. customthe pyrimidine was precipitated with 10 ml of 2 molar hydrochloric acid as an intensive yellow solid
  4. washThe solid was sequentially washed with water, ethanol and diethyl ether
  5. customm.p. greater >230° C.

Sources & evidence

ORD record
ord-450dc10b50984b4aa5ddbde196c4908c
Source dataset
uspto-grants-2001_12
Patent number
US06326327B1

Reaction notes

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