Chloroacetone → HCID 13060079, compound

HRID 560292Notes

Reaction equation

HRID 560292 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8](=[S:12])[NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].Cl[CH2:14][C:15](=O)[CH3:16].O=P(Cl)(Cl)Cl>CCO.CC#N>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:9]([C:10]=1[CH3:11])[C:15]([CH3:16])=[CH:14][S:12]2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 24813Phosphorus oxychlorideHCID 3824588MLS002639316

Product 1

HCID 13060079HCID 13060079, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-methyl-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester (5.37 mmol) and chloroacetone (6.44 mmol) in EtOH (10 mL) is heated at reflux for 150 min. The solvents are removed in vacuo and a solution of POCl3 (16.1 mmol) in MeCN (10 mL) is added. The mixture is stirred at reflux for 60 h, concentrated in vacuo and diluted with chloroform. Ice water is added and the mixture is neutralized by addition of Na2CO3. The layers are separated and the aq. layer is extracted with chloroform. The combined organic layers are dried over Na2SO4 and concentrated in vacuo to give a mixture of two regioisomers (see A.7.7) which are separated by FC (heptane to heptane/EtOAc 3/7). LC-MS: tR=0.71 min; [M+H]+=225.0.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 150 min
  3. customThe solvents are removed in vacuo
  4. temperatureat reflux for 60 h
  5. concentrationconcentrated in vacuo
  6. additiondiluted with chloroform
  7. additionIce water is added
  8. additionthe mixture is neutralized by addition of Na2CO3
  9. customThe layers are separated
  10. extractionthe aq. layer is extracted with chloroform
  11. dry with materialThe combined organic layers are dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customto give
  14. additiona mixture of two regioisomers (
  15. customare separated by FC (heptane to heptane/EtOAc 3/7)

Sources & evidence

ORD record
ord-5a12c35098a24035ac6a286b03fa95ae
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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