Diethyl (ethoxymethylene)malonate → HCID 178447935, compound

HRID 1463007Notes

Reaction equation

HRID 1463007 reaction equation
Cl.[CH2:2]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([NH2:13])=[NH:12])[CH2:7][CH2:6]1)[CH2:3][CH3:4].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.CC[O-].[Na+].[Na]>C(O)C>[OH:16][C:17]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:13]=[C:11]([C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]2)[N:12]=1

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 178448081HCID 178448081, compound

Product 1

HCID 178447935HCID 178447935, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

23.9 g of trans-4-propylcyclohexanecarboxamidine hydrochloride and 25.2 g of diethyl ethoxymethylene-malonate are added to a sodium ethylate solution prepared from 5.4 g of sodium and 210 ml of ethanol and the mixture is diluted with 150 ml of ethanol. The mixture is stirred at room temperature for 50 minutes and at boiling temperature for 50 minutes and, after cooling, evaporated in vacuo. The viscid residue is suspended in 600 ml of water and acidified with 60 ml of glacial acetic acid. Subsequently, the suspension is stirred for 1.5 hours in an ice-bath and suction filtered. The material on the suction filter is washed with water and dried at 50° C. in vacuo over potassium hydroxide. There are obtained 33 g of ethyl trans-4-hydroxy-2-(4-propylcyclohexyl)-5-pyrimidinecarboxylate; m.p. 156°-157° C.

Workup

  1. customfor 50 minutes
  2. temperatureafter cooling
  3. customevaporated in vacuo
  4. stirringSubsequently, the suspension is stirred for 1.5 hours in an ice-bath
  5. filtrationsuction filtered
  6. filtrationThe material on the suction filter
  7. washis washed with water
  8. dry with materialdried at 50° C. in vacuo over potassium hydroxide

Sources & evidence

ORD record
ord-b14ef1424a4540d083d671ec3dc49925
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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