Chloroform → HCID 20394584, compound

HRID 26052Notes

Reaction equation

HRID 26052 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](=[O:19])[N:13]([CH3:18])[C:14]([C:15]([OH:17])=O)=[C:10]3[CH2:9][N:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:6]=2[CH:27]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[OH-].[NH4+:35].C(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](=[O:19])[N:13]([CH3:18])[C:14]([C:15]([NH2:35])=[O:17])=[C:10]3[CH2:9][N:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:6]=2[CH:27]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 24819Phosphorus pentachlorideHCID 20394577HCID 20394577, compound

Product 1

HCID 20394584HCID 20394584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 3 g (0.0075 mole) of 8-chloro-6-(2-chlorophenyl)-1,2-dihydro-2-methyl-1-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-carboxylic acid in 90 ml of methylene chloride was cooled in an ice bath and treated with 1.9 g (0.009 mole) of phosphorus pentachloride in portions. Stirring in the cold under a drying tube was continued for 30 min. Ammonia was then bubbled into the cold solution for 5 min and stirring in the cold was continued 30 min. longer. Evaporation at reduced pressure gave a tan solid. The solid was stirred with 3N ammonium hydroxide and extracted with methylene chloride. An emulsion formed but was destroyed by filtering to remove some high melting solid. The methylene chloride layer was dried over sodium sulfate and evaporated to give a yellow solid which was recrystallized from benzene to give off-white needles with mp 158°-160°. Uv λ sh 215 mμ (ε=43000) max 272 (15500) sh 330 (2500); ir (CHCl3) 3510, 3400 cm-1 (NH2) 1703 (CO) 1685 (CONH2).

Workup

  1. temperaturewas cooled in an ice bath
  2. customAmmonia was then bubbled into the cold solution for 5 min
  3. stirringstirring in the cold
  4. waitwas continued 30 min.
  5. customEvaporation at reduced pressure
  6. customgave a tan solid
  7. extractionextracted with methylene chloride
  8. customAn emulsion formed
  9. customwas destroyed
  10. filtrationby filtering
  11. customto remove some high melting solid
  12. dry with materialThe methylene chloride layer was dried over sodium sulfate
  13. customevaporated
  14. customto give a yellow solid which
  15. customwas recrystallized from benzene
  16. customto give off-white needles with mp 158°-160°

Sources & evidence

ORD record
ord-84a0c15c4b624da08da56af5f4e583b0
Source dataset
uspto-grants-1979_04
Patent number
US04147875

Reaction notes

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