Potassium Iodide → HCID 68120563, compound

HRID 596378Notes

Reaction equation

HRID 596378 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][CH:18]=3)[C:6]=2[CH:23]=1.[I-].[K+].[CH3:26][CH:27]=[CH:28][CH2:29][NH2:30]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][NH:30][CH2:29][CH2:28][CH:27]=[CH2:26])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 304472-Buten-1-amineHCID 126123458-chloro-1-(chloromethyl)-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 68120563HCID 68120563, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 8-chloro-1-(chloromethyl)-6-phenyl-4-H-s-triazolo[4,3-a][1,4]benzodiazepine (1.37 g., 0.004 mole), potassium iodide (0.67 g., 0.004 mole), methylallylamine (0.84 g., 0.012 mole) and tetrahydrofuran (100 ml.) is kept at ambient temperature (25° C.) for 18 hours and 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 1.19 g of 8-chloro-1-[(allylmethylamino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 157°-160° C. The analytical sample has a melting point of 158° -164° C. Anal. calcd. for C21H20ClN5 : C, 66.75; H, 5.33; Cl, 9.38; N, 18.53. Found: C, 66.87; H, 5.46; Cl, 9.42; N, 18.67. Preparation 40 8-Chloro-1-[(allylmethylamino)methyl]-6-(o-chlorophenyl)-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-94a43f2af6ef4dadbc3a1cbcf17b0062
Source dataset
uspto-grants-1977_03
Patent number
US04010177

Reaction notes

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