Pyrrolidine → HCID 12666075, compound

HRID 848588Notes

Reaction equation

HRID 848588 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][NH:8][C:7](=S)[C:6]=2[CH:17]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 12666069HCID 12666069, compound

Product 1

HCID 12666075HCID 12666075, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 8-chloro-4,5-dihydro-1-methyl-6H-s-triazolo[4,3-a][1,4]benzodiazepine-6-thione (VIIIa)(2.65 g., 0.01 mole) and pyrrolidine (25 ml.) was refluxed under nitrogen for 10 hours, cooled, mixed with water and extracted with methylene chloride. The extract was washed with water, dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in methylene chloride/ethyl acetate, decolorized with charcoal (Darco) and concentrated until the product crystallized. The product was recrystallized from methylene chloride/acetate to give 1.43 g., melting point 223°-225° and 0.10 g., melting point 222°-225° of the titled compound (Ic)(51% yield). The analytical sample had: melting point 223°-225°; uv (EtOH) λ max 210.5 mμ (ε 41,050), 233 (sh 17,700), 287 (sh, 3450), 292 (3550). The ir and nmr spectra support the proposed structure.

Workup

  1. temperaturewas refluxed under nitrogen for 10 hours
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride/ethyl acetate
  8. concentrationconcentrated until the product
  9. customcrystallized
  10. customThe product was recrystallized from methylene chloride/acetate
  11. customto give 1.43 g

Sources & evidence

ORD record
ord-2a74a623b0a845418e2ea2d110d221fe
Source dataset
uspto-grants-1981_10
Patent number
US04296239

Reaction notes

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