Acetic Anhydride → 5-[3-(Acetyloxy)propylthio]imidazo[1,2-a]pyridine

HRID 1081732Notes

Reaction equation

HRID 1081732 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628785-[3-(Acetyloxy)propylthio]imidazo[1,2-a]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (2.00 g, 9.60 mmoles) and triethylamine (1.60 ml, 11.5 mmoles) in methylene chloride (50 ml) was added acetic anhydride (1.10 ml, 11.6 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 7.5 hours. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 2.40 g of the desired product (100%, brown oily product).

Workup

  1. stirringthe mixture was further stirred at room temperature for 7.5 hours
  2. washThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

Sources & evidence

ORD record
ord-95f6e3dcb1594530aba8c34dc62e08fd
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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