Acetic Acid → HCID 18917625, compound

HRID 234066Notes

Reaction equation

HRID 234066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:20][N:21]=[C:11]3[CH2:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C>ClCCl.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:20][N:21]=[C:11]3[CH2:10][NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18917622HCID 18917622, compound

Product 1

HCID 18917625HCID 18917625, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

6-(4-Chlorophenyl)-1-undecyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine (1.23 g) was dissolved in dichloromethane (10 ml) and acetic acid (5 ml) and zinc powder (540 mg) were added thereto with stirring. After stirring at room temperature for 6 hours, the mixture was washed with 5% aqueous sodium hydrogencarbonate and water. The reaction mixture was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and the oily substance obtained was crystallized from ethyl acetate to give 320 mg of 6-(4-chlorophenyl)-1-undecyl-4H,5H,6H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine, mp. 94°-95° C.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. washthe mixture was washed with 5% aqueous sodium hydrogencarbonate and water
  3. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customthe oily substance obtained
  8. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f1a53aeef9cf4bf7a7ed40ee66e4cca5
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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