Phosphorus oxychloride → HCID 13060078, compound

HRID 560296Notes

Reaction equation

HRID 560296 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:12]([C:13]=1[CH3:14])[CH:11](O)[CH2:10][S:9]2)=[O:5])[CH3:2].O=P(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:12]([C:13]=1[CH3:14])[CH:11]=[CH:10][S:9]2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13060114HCID 13060114, compound

Product 1

HCID 13060078HCID 13060078, compound

Procedure

3-hydroxy-5-methyl-2,3-dihydro-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester (4.00 mmol) is added to POCl3 (9.3 mL), stirred at reflux for 3 h and concentrated in vacuo. Chloroform and ice-water are added successively 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 the desired product which is purified by FC (heptane/EtOAc 1/1 to EtOAc). LC-MS: tR=0.66 min; [M+H]+=211.0.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. additionChloroform and ice-water are added successively
  4. additionthe mixture is neutralized by addition of Na2CO3
  5. customThe layers are separated
  6. extractionthe aq. layer is extracted with chloroform
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32e728b168ac4652be28013032e86911
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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