Chloroacetaldehyde → HCID 178503524, compound

HRID 1359437Notes

Reaction equation

HRID 1359437 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](O)[CH:6]=[C:5]([NH2:10])[N:4]=1.[C:11]([O-:14])(=O)[CH3:12].[Na+].ClCC=O>O>[CH3:1][S:2][C:3]1[NH:8][C:7]2[C:12]([N:10]=[CH:5][CH:6]=2)=[C:11]([OH:14])[N:4]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 517045Sodium AcetateHCID 178503503HCID 178503503, compound

Product 1

HCID 178503524HCID 178503524, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-(Methylthio)4-hydroxy-6-aminopyrimidine (3.1) (40 g) and sodium acetate (40 g, 2 eq.) were mixed with water (600 ml) and the slurry heated to 80° C. with vigorous stirring. To the mixture was then added chloroacetaldehyde (50 wt. % in water, 40 g, 1 eq.), slowly over 10 mins. The mixture turned yellow in colour and the solid mostly dissolved, before a new solid precipitated. After a further 30 mins, the mixture was allowed to cool overnight, then the solid was collected by filtration, washed well with water and then with acetone. Dried under vacuum at 50° C. to give (3.2), 8.7 g. δH (300MHz, DMSO-db); 2.49 (3H, s, SCH3), 6.33 (1H, m, H7), 6.89 (1H, m, H8), 11.74 and 12.03 (2×broad s, D2O exch.) ppm.

Workup

  1. dissolutionthe solid mostly dissolved, before a new solid
  2. customprecipitated
  3. temperatureto cool overnight
  4. filtrationthe solid was collected by filtration
  5. washwashed well with water
  6. customDried under vacuum at 50° C.

Sources & evidence

ORD record
ord-d07bbfd37bc3442ab61eb6841a4d3fa7
Source dataset
uspto-grants-2003_07
Patent number
US06600028B1

Reaction notes

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