m-Chloroperbenzoic acid → HCID 13343800, compound

HRID 745589Notes

Reaction equation

HRID 745589 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][S:20][C:21]2[NH:25][C:24]3[CH:26]=[C:27]4[C:31](=[CH:32][C:23]=3[N:22]=2)[CH2:30][CH2:29][CH2:28]4)=[N:17][CH:18]=1>C(OCC)(=O)C.C(Cl)Cl>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][S:20]([C:21]2[NH:25][C:24]3[CH:26]=[C:27]4[C:31](=[CH:32][C:23]=3[N:22]=2)[CH2:30][CH2:29][CH2:28]4)=[O:9])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13343798HCID 13343798, compound

Product 1

HCID 13343800HCID 13343800, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

50 ml of a 10% solution of m-chloroperbenzoic acid in ethyl acetate were added dropwise with intensive stirring and at 0°-5° C. to 6.7 g of 1,5,6,7-tetrahydro-2-[[(5-methyl-2-pyridyl)-methyl]thio]indeno(5,6-d)imidazole, dissolved in 200 ml of methylene chloride. After stirring at 0°-5° C. for 3 hours, the mixture was poured into 1 l of methylene chloride, it was washed twice with 250 g of 2N soda, then neutral with water, dried over sodium sulfate and evaporated in vacuo. 6.5 g of crude product were recrystallized from acetonitrile. There were obtained 4.6 g (65.1% of theory) of 1,5,6,7-tetrahydro-2-[[(5-methyl-2-pyridyl)methyl]sulfinyl]indeno(5,6-d)imidazole of melting point 190°-201° C.

Workup

  1. washwas washed twice with 250 g of 2N soda
  2. dry with materialneutral with water, dried over sodium sulfate
  3. customevaporated in vacuo
  4. custom6.5 g of crude product were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c35353474fde4916bce60ccb47c53705
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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