Ethyl Acetate → HCID 178481182, compound

HRID 265331Notes

Reaction equation

HRID 265331 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][C:19]2[CH:25]=[C:24](C(=S)N)[CH:23]=[CH:22][C:20]=2[N:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])O.[Na+].BrC[C:36](=O)[CH3:37].C(OCC)(=O)C>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][C:19]2[CH:25]=[C:24]([SH:18]3[CH:37]=[CH:36][N:21]([CH3:20])[CH2:17]3)[CH:23]=[CH:22][C:20]=2[N:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11715BromoacetoneHCID 516892Sodium BicarbonateHCID 99317771-(2,4-Difluorophenyl)-1-(6-thiocarbamoylbenzothiazol-2-yl)-2-(1H-1,2,4-triazol-yl)ethanol

Product 1

HCID 178481182HCID 178481182, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(2,4-Difluorophenyl)-1-(6-thiocarbamoylbenzothiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (219 mg) was dissolved in ethanol (2 ml), and sodium hydrogencarbonate (42 mg) and bromoacetone (46 μl) were added to the solution. The resultant mixture was heated at 60° C. for 3 hours. Ethyl acetate and water were added to the liquid reaction mixture to separate liquid layers. An organic layer was washed with saline and then dried, and the solvent was distilled out. The residue was subjected to column chromatography on silica gel (eluting solvent: chloroform:methanol=100:1), thereby obtaining the intended compound (114 mg). Melting point: 213°-215° C.

Workup

  1. customto separate liquid layers
  2. washAn organic layer was washed with saline
  3. customdried
  4. distillationthe solvent was distilled out

Sources & evidence

ORD record
ord-75df2d96c21b4c178df6f433653c1e8b
Source dataset
uspto-grants-1997_07
Patent number
US05648372

Reaction notes

Loading…