4-Chlorobenzoyl chloride → HCID 15135977, compound

HRID 1086157Notes

Reaction equation

HRID 1086157 reaction equation
[OH:1][CH:2]([C:4]1[S:13][C:12]2[N:11]3[C:14]([CH3:17])=[N:15][N:16]=[C:10]3[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[C:6]=2[CH:5]=1)[CH3:3].[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>N1C=CC=CC=1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:1][CH:2]([C:4]2[S:13][C:12]3[N:11]4[C:14]([CH3:17])=[N:15][N:16]=[C:10]4[CH2:9][N:8]=[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[C:6]=3[CH:5]=2)[CH3:3])=[O:31])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 15135976HCID 15135976, compound

Product 1

HCID 15135977HCID 15135977, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.1 g of 2-(1-hydroxyethyl)-4-(2-methyl-phenyl)-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine dissolved in 14 ml of pyridine is added 0.63 g of 4-chlorobenzoyl chloride under ice-cooling and then stirred for 2.5 hours. After completion of the reaction, the mixture is concentrated under reduced pressure and the residue is dissolved in 50 ml of chloroform. The solution is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering off, the filtrate is concentrated under reduced pressure and the residue is subjected to chromatography on silica gel and eluted with chloroform-methanol (100:1-100:3). The objective fraction is concentrated under reduced pressure to give 0.5 g of 2-(1-(4-chlorobenzoyl)oxyethyl)-4-(2-methylphenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine as an amorphous powder.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. concentrationthe mixture is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in 50 ml of chloroform
  5. washThe solution is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. washeluted with chloroform-methanol (100:1-100:3)
  10. concentrationThe objective fraction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d0d59ba4b004a2eb70b7ec7e66a1c23
Source dataset
uspto-grants-1991_07
Patent number
US05028603

Reaction notes

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