Acetic Acid → HCID 19743673, compound

HRID 260749Notes

Reaction equation

HRID 260749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH2:14][C:15](OC)=[O:16])=[CH:12][N:11]=[C:10]1[S:19][CH2:20][CH2:21][CH3:22].CO.C(O)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([CH2:14][CH2:15][OH:16])=[CH:12][N:11]=[C:10]1[S:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 22400407HCID 22400407, compound

Product 1

HCID 19743673HCID 19743673, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-[1-{(2-chlorophenyl)methyl}-2-propylthio-1H-imidazol-5-yl]acetate (2.1 g, 6.2 mmol) in dry tetrahydrofuran (150 mL) was cooled to -78° C. for 1.5 hours and at ambient temperature for 18 hours. Methanol was added followed by 5% aqueous acetic acid. The mixture was concentrated in vacuo, the residue was extracted with methylene chloride, and the organic extract was washed with 5% aqueous sodium carbonate solution, dried, and concentrated to give 2.33 g of crude product. This was chromatographed over silica gel with ethyl acetate to give 1.6 g (84%) of 1-[(2-chlorophenyl)methyl]-5-(2-hydroxy)ethyl-2-propylthio- 1H-imidazole as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionthe residue was extracted with methylene chloride
  3. extractionthe organic extract
  4. washwas washed with 5% aqueous sodium carbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customto give 2.33 g of crude product
  8. customThis was chromatographed over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-86ec1265809848daad26827eea7d6a4b
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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