Ethanol → Ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinylacetate

HRID 255728Notes

Reaction equation

HRID 255728 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])#N.S(=O)(=O)(O)O.[CH2:31]([OH:33])[CH3:32].C(=O)([O-])[O-:35].[Na+].[Na+]>O.C(Cl)(Cl)Cl>[CH3:10][C:9]1[N:8]=[C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:6]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:4]=1[CH2:3][C:1]([O:33][CH2:31][CH3:32])=[O:35]

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 99967205-Cyanomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 10362221Ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 5 -cyanomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (5 g), conc. sulfuric acid (12 g) and ethanol (50 ml) was gently refluxed for 72 hours. The reaction mixture was poured into a suspension of chloroform (200 ml) and water (100 ml), and then adjusted to pH 8.5 with 10% aqueous sodium carbonate solution. The separated organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated in vacuo. The residual substance was recrystallized from diethyl ether-n-hexane to give ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinylacetate (3.7 g).

Workup

  1. temperaturewas gently refluxed for 72 hours
  2. washThe separated organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residual substance was recrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-f304a988f106450d991ff6dd6ce7b1c8
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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