Hydrochloric Acid → HCID 22638562, compound

HRID 2416191Notes

Reaction equation

HRID 2416191 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17]C)=[O:16])[N:13]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO.C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([OH:17])=[O:16])[N:13]=2)[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22638557HCID 22638557, compound

Product 1

HCID 22638562HCID 22638562, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-[2-(2-ethyl-4-pyridyl)-1,3-thiazol-4-yl]acetate (Step a, 0.5 g, 1.9 mmol) and LiOH (2 N, 5.0 mL) in THF (5 mL) and MeOH (2 mL) was stirred at RT for 7 h. HCl (aq. 1 N) was added to adjust the reaction mixture to pH ˜2. The solution was evaporated and the resulting residue was partitioned between EtOAc (20 mL) and H2O (20 mL). The layers were separated and the aqueous layer was extracted again with EtOAc (2×20 mL). The organic layers were combined, dried (Na2SO4), and concentrated to afford a solid, which was suspended in CH2Cl2 and filtered to give the compound as a white solid. MS m/z: 249 (M+1). Calc'd for C12H12N2O2S. 248.06.

Workup

  1. customThe solution was evaporated
  2. customthe resulting residue was partitioned between EtOAc (20 mL) and H2O (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted again with EtOAc (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford a solid, which
  8. filtrationfiltered

Sources & evidence

ORD record
ord-aa18ed30a6d94b47b5490eacc84c3228
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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