Ethanol → HCID 178493619, compound

HRID 1200232Notes

Reaction equation

HRID 1200232 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]=1.C([OH:22])C.[Cl:23]C1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[ClH:23].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:10])=[O:22])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 70297m-Chloroperbenzoic acidHCID 178493617HCID 178493617, compound

Product 1

HCID 178493619HCID 178493619, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Two grams of 2-(2-methoxy-4-methylmercaptophenyl)imidazo[4,5-c]pyridine were dissolved in 50 ml. of hot ethanol and then cooled. One hundred milliliters of chloroform were added and the solution was cooled to -30° to -40° C. by means of an external cooling bath. A solution of 1.455 g. of 85% meta-chloroperbenzoic acid in 10 ml. of chloroform was added to the solution over a one hour period. The solution was stirred for three additional hours at -30° to -40° C. The reaction was then warmed to room temperature and evaporated in vacuo. The resulting foam was dissolved in 20 ml. of dimethylformamide after which were added 1.3 ml. of concentrated hydrochloric acid. Diethyl ether was added to the cloud point and the solution was stirred for 30 minutes. The suspension was then chilled and filtered affording 2.1 g. of the title product as brown crystals, m.p. about 210°-212° C.

Workup

  1. temperaturethe solution was cooled to -30° to -40° C. by means of an external cooling bath
  2. customevaporated in vacuo
  3. dissolutionThe resulting foam was dissolved in 20 ml
  4. additionof dimethylformamide after which were added 1.3 ml
  5. additionDiethyl ether was added to the cloud point
  6. stirringthe solution was stirred for 30 minutes
  7. temperatureThe suspension was then chilled
  8. filtrationfiltered
  9. customaffording 2.1 g

Sources & evidence

ORD record
ord-c16a7051cf67415dabc36fca4107670b
Source dataset
uspto-grants-1990_02
Patent number
US04904785

Reaction notes

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