Diethyl (ethoxymethylene)malonate → HCID 178442344, compound

HRID 461305Notes

Reaction equation

HRID 461305 reaction equation
Cl.[CH2:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH2:22])=[NH:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:23]([O:25][C:26](=[O:37])[C:27](=[CH:33]OCC)[C:28](OCC)=[O:29])[CH3:24].CC[O-].[Na+].[Na]>C(O)C>[CH2:23]([O:25][C:26]([C:27]1[C:28]([OH:29])=[N:21][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:9][CH:10]=3)=[CH:19][CH:18]=2)=[N:22][CH:33]=1)=[O:37])[CH3:24]

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15564018HCID 15564018, compound

Product 1

HCID 178442344HCID 178442344, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.0 g. of 4'-n-hexyl-4-biphenyl-amidine hydrochloride and 4.9 g. of ethoxymethylene-malonic acid diethyl ester is stirred in a sodium ethylate solution, from 0.867 g. of sodium and 80 ml. of ethanol, for 40 minutes at room temperature and 40 minutes under reflux. After this, the yellow reaction mixture is evaporated in vacuo and the residue is suspended in 95 ml. of water and acidified with 15 ml. of glacial acetic acid. Filtering, washing with water and drying yields crude 2-(4'-n-hexyl-4-biphenylyl)-4-hydroxy-pyrimidine-5-carboxylic acid ethyl ester which can be sublimed at 185° in high vacuum for purification, m.p. 218.0°.

Workup

  1. additionA mixture of 6.0 g
  2. temperature40 minutes under reflux
  3. customAfter this, the yellow reaction mixture is evaporated in vacuo
  4. filtrationFiltering
  5. washwashing with water
  6. customdrying

Sources & evidence

ORD record
ord-ad930b4c0eef4bc4863961bf45698dc4
Source dataset
uspto-grants-1977_12
Patent number
US04062798

Reaction notes

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