Hydrochloric Acid → HCID 20483471, compound

HRID 1764336Notes

Reaction equation

HRID 1764336 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH:13]([CH2:22][OH:23])[CH2:14][O:15][C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1.Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][CH:13]([OH:12])[CH2:14][O:15][C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 204834113-[(Pyrimidin-2-yl)oxy]propane-1,2-diol

Product 1

HCID 20483471HCID 20483471, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

13.6 g of p-toluenesulphonyl chloride are introduced over the course of 15 minutes, whilst stirring, into a solution of 11.8 g of 2-(2',3'-dihydroxy-propoxy)-pyrimidine in 18 ml of pyridine which is cooled to -10° C. The reaction mixture is kept at 0° C. for 15 hours. Ice is then added followed by 20 ml of 6 N hydrochloric acid introduced whilst stirring. The mixture is then twice extracted with 150 ml of methylene chloride at a time. The extracts are washed with sodium bicarbonate solution, dried over sodium sulphate and evaporated. 2-(3'-p-Toluenesulphonyloxy-2'-hydroxy-propoxy)-pyrimidine is obtained as a yellowish oil.

Workup

  1. additionIce is then added
  2. additionintroduced
  3. extractionThe mixture is then twice extracted with 150 ml of methylene chloride at a time
  4. washThe extracts are washed with sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-c56e75a75f1144e99aff39c1e951efd6
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

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