Acetic Acid → HCID 21449000, compound

HRID 597083Notes

Reaction equation

HRID 597083 reaction equation
[NH2:1][CH:2]([CH3:26])[CH2:3][C:4]1[N:8]2[C:9]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])=[N:12][CH2:13][C:7]2=[N:6][N:5]=1.C=O.[C:29](O)(=O)C.C([BH3-])#N.[Na+]>C(#N)C>[CH3:29][NH:1][CH:2]([CH3:26])[CH2:3][C:4]1[N:8]2[C:9]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])=[N:12][CH2:13][C:7]2=[N:6][N:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12612404HCID 12612404, compound

Product 1

HCID 21449000HCID 21449000, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.001 mole of 1-(2-aminopropyl)-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine in acetonitrile is successively treated with 0.001 mole each of formaldehyde, acetic acid and sodium cyanoborohydride at room temperature. The mixture is concentrated in vacuo and the residue treated with 25% aqueous ethylene diamine (5 ml.) and methanol (10 ml.) and refluxed under nitrogen for 2 hours. This mixture is concentrated and the residue mixed with water and extracted with chloroform. The chloroform extracts were filtered, evaporated, and crystallized to give 1-[2-(methylamino)propyl]-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionthe residue treated with 25% aqueous ethylene diamine (5 ml.) and methanol (10 ml.)
  3. temperaturerefluxed under nitrogen for 2 hours
  4. concentrationThis mixture is concentrated
  5. additionthe residue mixed with water
  6. extractionextracted with chloroform
  7. filtrationThe chloroform extracts were filtered
  8. customevaporated
  9. customcrystallized

Sources & evidence

ORD record
ord-392dc933f9344978ba0e6895bae20e70
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

Loading…