1,3-Dichloroacetone → HCID 22478818, compound

HRID 736485Notes

Reaction equation

HRID 736485 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[S:3])[NH2:2].[Cl:14][CH2:15][C:16]([CH2:18]Cl)=O>C1COCC1>[Cl:14][CH2:15][C:16]1[N:2]=[C:1]([CH2:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[S:3][CH:18]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 22478982HCID 22478982, compound

Product 1

HCID 22478818HCID 22478818, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 (729 mg, 3.73 mmol) and 1,3-dichloroacetone (474 mg, 3.73 mmol) in THF (30 ml) was stirred at 40° C. during 48 h. The solvent was evaporated then the residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2) to afford the title compound (827 mg, 83% yield) as a white solid. 1H NMR (DMSO) δ (ppm): 12.93 (bs, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.63 (s, 1H), 7.46 (d, J=8.1 Hz, 2H), 4.78 (s, 2H), 4.42 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4a7a316421d3480c8bd543d3304665cc
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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