Ethanol → HCID 19934739, compound

HRID 37100Notes

Reaction equation

HRID 37100 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([OH:10])=[O:9])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[NH:3]1.OS(O)(=O)=O.O=S(Cl)Cl.[CH2:28](O)[CH3:29]>>[O:1]=[C:2]1[NH:7][C:6]([C:8]([O:10][CH2:28][CH3:29])=[O:9])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[NH:3]1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 19934769HCID 19934769, compound

Product 1

HCID 19934739HCID 19934739, compound

Procedure

The required starting compound may also be prepared as follows: 1.8 g of 2,6-dioxo-5-phenoxy-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid (preparation described in: Khim Geterotsikl. Soedin., 1974, p1527) are emulsified in 65 ml of ethanol, 0.92 ml of conc. H2SO4 and 0.92 ml of SOCl2 are subsequently added and the mixture is heated at reflux for 12 hrs. Subsequently, the mixture is concentrated on a rotary evaporator and the seperated solid is filtered off under suction and chromatographed on silica gel (eluent: CH2Cl2 /ether: 3/1). There are obtained 520 mg of ethyl 2,6-dioxo-5-phenoxy-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate as a solid. MS: M=276.

Workup

  1. custommay also be prepared
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 12 hrs
  4. concentrationSubsequently, the mixture is concentrated on a rotary evaporator
  5. filtrationthe seperated solid is filtered off under suction
  6. customchromatographed on silica gel (eluent: CH2Cl2 /ether: 3/1)

Sources & evidence

ORD record
ord-5405dbf97ead4612b80d3be6661c4a48
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Reaction notes

Loading…