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

HRID 464122노트

반응식

HRID 464122 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45525a606d9a4dfda4be3b9345eb677f
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04546179

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