Pyridine → HCID 14649623, compound

HRID 1165422Notes

Reaction equation

HRID 1165422 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:20]2[CH:21]=[C:22]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=3)[S:23][C:19]=2[N:18]2[C:34]([CH3:37])=[N:35][N:36]=[C:17]2[CH:16]([CH3:38])[N:15]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:20]2[CH:21]=[C:22]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][CH:27]=3)[S:23][C:19]=2[N:18]2[C:34]([CH3:37])=[N:35][N:36]=[C:17]2[CH:16]([CH3:38])[N:15]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 14649622HCID 14649622, compound

Product 1

HCID 14649623HCID 14649623, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 15 g of dry sellaite and 12 g of dry pyridine in 150 ml of methylene chloride is added 7.4 g of chromic anhydride under ice-cooling with stirring and then stirred for 20 minutes. To the mixture is added a solution of 7 g of 4-(2-chlorophenyl)-2-[2(4-hydroxymethylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, which was prepared by Example 1, in 20 ml of methylene chloride dropwise with stirring and stirred for an hour. The methylene chloride layer is separated by filtration and the sellaite is well washed with chloroform. The mixture of the washings and the methylene chloride solution is thoroughly washed with water and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the resulting oil is subjected to chromatography on silica gel to give 4 g of 4-(2-chlorophenyl)-2-[2-(4-formylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine.

Workup

  1. temperaturecooling
  2. stirringstirred for 20 minutes
  3. stirringwith stirring
  4. stirringstirred for an hour
  5. customThe methylene chloride layer is separated by filtration
  6. washthe sellaite is well washed with chloroform
  7. additionThe mixture of the washings
  8. washthe methylene chloride solution is thoroughly washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter separating by filtration
  11. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-9f73bc7a0326442682489e6e31494793
Source dataset
uspto-grants-1990_03
Patent number
US04910194

Reaction notes

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