2-Mercaptoethanol → HCID 20080435, compound

HRID 1681883Notes

Reaction equation

HRID 1681883 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]=[O:8])[CH:4]=[N:3][CH:2]=1.C1(C)C=C[C:12]([S:15](O)(=O)=O)=[CH:11]C=1.SCCO>>[O:8]1[CH2:11][CH2:12][S:15][CH:7]1[C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 2761034Pyrimidine-5-carboxaldehyde

Product 1

HCID 20080435HCID 20080435, compound

Procedure

Pyrimidine-5-carboxaldehyde (1 g, 9.25 mmol), p-toluene sulfonic acid (0.176 g, 0.95 mmol) and 2-mercaptoethanol (0.65 ml, 9.25 mmol) were all put in a 50 ml round bottomed flask, fitted with a condenser, drying tube and a Dean-stark trap. Toluene (30 ml) was added and the mixture refluxed with stirring overnight, cooled to room temperature and excess toluene evaporated in vacuo. Saturated sodium carbonate 10 ml was added and extracted with chloroform (7×10 ml). The extract was dried over MgSO4, filtered and the solvent evaporated in vacuo to 1.73 g (115%) crude yellow oil. TLC (silica; chloroform/methanol 9.8:0.2) indicated the product and some impurities.

Workup

  1. customall put in a 50 ml round bottomed flask
  2. customfitted with a condenser
  3. customdrying tube and a Dean-stark trap
  4. additionToluene (30 ml) was added
  5. temperaturethe mixture refluxed
  6. customexcess toluene evaporated in vacuo
  7. additionSaturated sodium carbonate 10 ml was added
  8. extractionextracted with chloroform (7×10 ml)
  9. dry with materialThe extract was dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent evaporated in vacuo to 1.73 g (115%) crude yellow oil

Sources & evidence

ORD record
ord-539f42ea214c40f9abf146753cb67e2c
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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