Pivaloyl chloride → HCID 15135987, compound

HRID 1086160Notes

Reaction equation

HRID 1086160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH:18]([OH:20])[CH3:19])[S:17][C:13]=2[N:12]2[C:21]([CH3:24])=[N:22][N:23]=[C:11]2[CH2:10][N:9]=1.[C:25](Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH:18]([O:20][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:19])[S:17][C:13]=2[N:12]2[C:21]([CH3:24])=[N:22][N:23]=[C:11]2[CH2:10][N:9]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 15135972alpha-Hydroxyetizolam

Product 1

HCID 15135987HCID 15135987, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3 g of 4-(2-chlorophenyl)-2-(1-hydroxyethyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine dissolved in 30 ml of pyridine is added 1 g of pivaloyl chloride under ice-cooling and then stirred overnight. After completion of the reaction, the mixture is concentrated under reduced pressure and the residue is dissolved in 30 ml of ethyl acetate. 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 followed by crystallization from ligroinethyl acetate to give 1.1 g of 4-(2-chlorophenyl)-9-methyl-2(1-pivaloyloxyethyl)-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine as crystals, melting at 148°-151° C.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. concentrationthe mixture is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in 30 ml of ethyl acetate
  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
  11. customfollowed by crystallization from ligroinethyl acetate

Sources & evidence

ORD record
ord-fb95fc14ea0c4df2b960e9075cc3b4c8
Source dataset
uspto-grants-1991_07
Patent number
US05028603

Reaction notes

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