Hexamethylenetetramine → Nitrazepam

HRID 1973059

반응식

HRID 1973059 반응식
C1N2CN3CN(C2)C[N:2]1C3.Cl[CH2:12][C:13]([NH:15][C:16]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:17]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)=[O:14]>C(O)C>[N+:30]([C:27]1[CH:28]=[CH:29][C:16]2[NH:15][C:13](=[O:14])[CH2:12][N:2]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]=2[CH:26]=1)([O-:32])=[O:31]

참가 물질

4

반응물 2

HCID 4101HexamethylenetetramineHCID 88706N-(2-Benzoyl-4-nitrophenyl)-2-chloroacetamide

생성물 1

HCID 4506Nitrazepam

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a 2-liter, 4-necked flask equipped with a stirrer, a reflux condenser and an ammonia tube, there was added 600 ml. of ethanol and 37.9 g. of hexamethylenetetramine with stirring. Ammonia was bubbled through the resultant reaction medium with stirring until reflux temperature was reached. Then there was carefully added to the refluxing solution 40.0 g. of 2-chloroacetamido-5-nitro benzophenone. Ammonia is steadily bubbled into the reaction mixture while continuing to reflux for three hours. The resultant solution was cooled, evaporated to dryness at 50° C. The residue was dissolved in 300 ml. of toluene. 0.3 G. of paratoluene sulfonic acid was added to the resultant solution. The solution was heated to reflux. The refluxing was continued for 1 hour. The reaction medium was then permitted to cool to room temperature. The product which separated was filtered off, washed with water and dried. This material was taken up in 435 ml. of methylene chloride. It was then filtered through Hyflo. Upon the addition of 90 ml. of 3N nitric acid to the filtrate, crystals appeared. They were filtered off, washed with methylenechloride and dried for 15 minutes. The crystals were added to 1 liter of water with stirring. Ammonium hydroxide was then carefully added to the resultant medium until a pH of about 8 was reached. After stirring the resultant medium for 1/2 hours, the crystalline precipitate which formed were filtered off, washed with cold water and dried at 80° for 8 hours yielding 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one of melting point 217°-219° .

후처리

  1. customTo a 2-liter, 4-necked flask equipped with a stirrer, a reflux condenser and an ammonia tube
  2. additionthere was added 600 ml
  3. customAmmonia was bubbled through the resultant
  4. customreaction medium
  5. temperatureuntil reflux temperature
  6. customAmmonia is steadily bubbled into the reaction mixture
  7. temperatureto reflux for three hours
  8. temperatureThe resultant solution was cooled
  9. customevaporated to dryness at 50° C
  10. dissolutionThe residue was dissolved in 300 ml
  11. additionof paratoluene sulfonic acid was added to the resultant solution
  12. temperatureThe solution was heated to reflux
  13. customThe product which separated
  14. filtrationwas filtered off
  15. washwashed with water
  16. customdried
  17. filtrationIt was then filtered through Hyflo
  18. additionUpon the addition of 90 ml
  19. filtrationThey were filtered off
  20. washwashed with methylenechloride
  21. customdried for 15 minutes
  22. additionThe crystals were added to 1 liter of water
  23. stirringwith stirring
  24. additionAmmonium hydroxide was then carefully added to the resultant medium until a pH of about 8
  25. stirringAfter stirring the resultant medium for 1/2 hours
  26. customthe crystalline precipitate which formed
  27. filtrationwere filtered off
  28. washwashed with cold water
  29. customdried at 80° for 8 hours

출처 및 근거

ORD 기록
ord-d6a83609384a4523847783aa880198c7
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03996209

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