Acetic Acid → HCID 21562359, compound

HRID 1580649Notes

Reaction equation

HRID 1580649 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][CH2:13][C:14]#CC)[CH2:9][N:8]=[C:7]([C:17]3[C:22](F)=[CH:21][CH:20]=[CH:19][C:18]=3F)[C:6]=2[CH:25]=1.[C:26]([OH:29])(=O)[CH3:27].[CH:30](O)=O.O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:27]([CH:26]=[O:29])=[C:13]([CH3:14])[N:12]=[C:10]3[CH:9]([CH3:30])[N:8]=[C:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 962WaterHCID 178448837HCID 178448837, compound

Product 1

HCID 21562359HCID 21562359, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 0.02 mole of 7-chloro-3-methyl-5-phenyl-2-[(1-methyl-2-propynyl)amino]-3H-1,4benzodiazepine (IV), 20 ml. of acetic acid, 20 ml. of 88% formic acid and 1.5 ml of water at ambient temperature is treated, dropwise, with 160 ml. of a 5% aqueous solution of mercuric acetate. The mixture is then stirred at room temperature for about 3 hours, poured into ice water and then extracted with chloroform. The extract thus obtained is washed with water and then concentrated in vacuo. The residue thus obtained is suspended in hot ethyl acetate and filtered. The filtrate is concentrated and chromatographed on silica gel with 50% ethyl acetate-hexanes to give 8-chloro-6-phenyl-2,4-dimethyl-4H-imidazo[1,2-a][1,4]benzodiazepine-1-carboxaldehyde.

Workup

  1. extractionextracted with chloroform
  2. extractionThe extract thus
  3. customobtained
  4. washis washed with water
  5. concentrationconcentrated in vacuo
  6. customThe residue thus obtained
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated
  9. customchromatographed on silica gel with 50% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-e297c97884c74ec09a6bbdb300443c35
Source dataset
uspto-grants-1976_01
Patent number
US03933794

Reaction notes

Loading…