N,N-Dimethylaniline → HCID 178475913, compound

HRID 704512Notes

Reaction equation

HRID 704512 reaction equation
[CH3:1]N(C)C1C=CC=CC=1.[C:10]([O:13][CH2:14][C:15]1[N:29]=[C:18]2[N:19]=[C:20]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:21]=[C:22]([OH:23])[N:17]2[N:16]=1)(=[O:12])[CH3:11].C(Cl)(Cl)Cl>P(Cl)(Cl)(Cl)=O>[C:10]([O:13][CH2:14][C:15]1([CH3:1])[N:29]=[C:18]2[N:19]=[C:20]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:21]=[C:22]([OH:23])[N:17]2[NH:16]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6212ChloroformHCID 178475879HCID 178475879, compound

Product 1

HCID 178475913HCID 178475913, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
50 °C

Procedure

In 300 ml of phosphorus oxychloride was added dropwise 28 ml of N,N-dimethylaniline, and 30.5 g of 2,5-bis(acetoxymethyl)-7-hydroxy-s-triazolo[1,5-a]pyrimidine was added to the mixture and the mixture was stirred at 50 ° C. for 1.5 hours. An oily residue obtained by removing phosphorus oxychloride was dissolved in 500 ml of chloroform and ice-cooled. After addition of crushed ice and water to the mixture and stirring thereof, a chloroform layer was separated, washed with water and dried over anhydrous magnesium sulfate. Then, the mixture was condensed. This was applied to a silica gel column chromatography (eluent chloroform) and fractions containing the title compound were condensed to obtain 14 g of the title compound as an oily product.

Workup

  1. additionwas added to the mixture
  2. customAn oily residue obtained
  3. customby removing phosphorus oxychloride
  4. dissolutionwas dissolved in 500 ml of chloroform
  5. temperatureice-cooled
  6. additionAfter addition of crushed ice and water to the mixture
  7. stirringstirring
  8. customa chloroform layer was separated
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customcondensed

Sources & evidence

ORD record
ord-6ad9e34d8a1c4e96a6a048eb22ebb314
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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