2-Amino-4,6-dimethyl pyrimidine → N-(2-Chlorobenzene-1-sulfonyl)-N'-(4,6-dimethylpyrimidin-2-yl)carbamimidic acid

HRID 464122Notes

Reaction equation

HRID 464122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[O-:12][C:13]#[N:14].[K+].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:14][C:13]([NH:24][C:19]1[N:20]=[C:21]([CH3:23])[CH:22]=[C:17]([CH3:16])[N:18]=1)=[O:12])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 11378442Potassium cyanate

Product 1

HCID 182458N-(2-Chlorobenzene-1-sulfonyl)-N'-(4,6-dimethylpyrimidin-2-yl)carbamimidic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A slurry of 23.8 g (0.10 mole) 2-chlorobenzenesulfonyl chloride, 16.2 g (0.2 mole) potassium cyanate, 15.5 g (0.11 moles) 4,6-dimethyl-2-pyrimidinamine in 150 ml acetonitrile was stirred at reflux for 5 hours. The reaction was cooled to 25° and filtered. The solids were dissolved in water, filtered, and the filtrate acidified to give a solid A. The reaction filtrate was distilled in vacuo to remove solvent. The residue and Solid A were combined, dissolved in 200 ml of 5% sodium hydroxide and extracted with methylene chloride. The aqueous layer was then acidified, the solids collected, washed with water and dried to give 18.9 g (50.6% of theory) of the title compound. The m.p. and IR spectrum of the title compound were identical to those of an authentic sample prepared as described in U.S. Pat. No. 4,169,719.

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureThe reaction was cooled to 25°
  3. filtrationfiltered
  4. dissolutionThe solids were dissolved in water
  5. filtrationfiltered
  6. customto give a solid A
  7. distillationThe reaction filtrate was distilled in vacuo
  8. customto remove solvent
  9. dissolutiondissolved in 200 ml of 5% sodium hydroxide
  10. extractionextracted with methylene chloride
  11. customthe solids collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-45525a606d9a4dfda4be3b9345eb677f
Source dataset
uspto-grants-1985_10
Patent number
US04546179

Reaction notes

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