Potassium Iodide → HCID 21437258, compound

HRID 596377Notes

Reaction equation

HRID 596377 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15]Cl)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:6]=2[CH:24]=1.[I-].[K+].[CH2:27]([NH2:30])[CH:28]=[CH2:29]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][NH:30][CH2:27][CH:28]=[CH2:29])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 7853AllylamineHCID 126123488-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

Product 1

HCID 21437258HCID 21437258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 8-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (0.004 mole), potassium iodide (0.67 g., 0.004 mole), allylamine (0.84 g., 0.012 mole) and tetrahydrofuran (100 ml.) is kept at ambient temperature (25° C.) for 18 hours and then concentrated in vacuo. The residue is mixed with water and extracted with methylene chloride. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is crystallized from ethyl acetate-Skellysolve B hexanes to give 8-chloro-1-[(allylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine. Preparation 39 8-Chloro-1-[(allylmethylamino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Workup

  1. customis kept at ambient temperature
  2. custom(25° C.)
  3. customfor 18 hours
  4. concentrationconcentrated in vacuo
  5. additionThe residue is mixed with water
  6. extractionextracted with methylene chloride
  7. washThe extract is washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue is crystallized from ethyl acetate-Skellysolve B hexanes

Sources & evidence

ORD record
ord-ede7f6053cdb4eb791d03fe8a18f627b
Source dataset
uspto-grants-1977_03
Patent number
US04010177

Reaction notes

Loading…