Thionyl Chloride → Deximafen

HRID 1576840

반응식

HRID 1576840 반응식
S(Cl)(Cl)=O.O[CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][NH:8][C:9]1[NH:10][CH2:11][CH2:12][N:13]=1>>[C:14]1([CH:6]2[N:13]3[CH2:12][CH2:11][NH:10][C:9]3=[N:8][CH2:7]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 103775alpha-(((4,5-Dihydro-1H-imidazol-2-yl)amino)methyl)benzyl alcohol

생성물 1

HCID 163316Deximafen

실험 절차

To 80 parts thionylchloride (previously cooled to 0°C.) are added 10.15 parts 2-(β-hydroxy-phenethyl-amino)-2-imidazoline. After the addition is complete, the whole is stirred for 30 minutes at room temperature and further stirred and refluxed for 15 minutes. The solvent is evaporated. The residue is dissolved in 40 parts toluene and evaporated again. This treatment is repeated by using 40 parts methanol. The residue is then dissolved in 40 parts 2-propanol. To this solution is added a solution of 1.15 parts sodium metal in 40 parts 2-propanol. The whole is stirred and refluxed for one hour. The solvent is evaporated. The residue is dissolved in 150 parts water. The solution is filtered. The filtrate is alkalized with ammonium hydroxide and extracted three times with 40 parts ether and three times with 75 parts chloroform. The combined extracts are dried over potassium carbonate and evaporated. The solid residue is recrystallized from a mixture of 16 parts acetone and 16 parts 4-methyl-2-pentanone, yielding 2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole; m.p. 167°-169.5°C.

후처리

  1. additionAfter the addition
  2. stirringfurther stirred
  3. temperaturerefluxed for 15 minutes
  4. customThe solvent is evaporated
  5. dissolutionThe residue is dissolved in 40 parts toluene
  6. customevaporated again
  7. dissolutionThe residue is then dissolved in 40 parts 2-propanol
  8. additionTo this solution is added a solution of 1.15 parts sodium metal in 40 parts 2-propanol
  9. stirringThe whole is stirred
  10. temperaturerefluxed for one hour
  11. customThe solvent is evaporated
  12. dissolutionThe residue is dissolved in 150 parts water
  13. filtrationThe solution is filtered
  14. extractionextracted three times with 40 parts ether and three times with 75 parts chloroform
  15. dry with materialThe combined extracts are dried over potassium carbonate
  16. customevaporated
  17. customThe solid residue is recrystallized from a mixture of 16 parts acetone and 16 parts 4-methyl-2-pentanone

출처 및 근거

ORD 기록
ord-246d6176e7fb40109669979edcff3aca
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03983133

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