m-Chloroperbenzoic acid → HCID 13343782, compound

HRID 1583774Notes

Reaction equation

HRID 1583774 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:36])[C:24]2[C:16](=[CH:17][C:18]3[NH:19][C:20]([S:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)=[N:21][C:22]=3[CH:23]=2)[C:15]([CH3:34])([CH3:33])[C:14]1=[O:35]>C(OCC)(=O)C.C(Cl)Cl>[CH3:12][C:13]1([CH3:36])[C:24]2[C:16](=[CH:17][C:18]3[NH:19][C:20]([S:25]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)=[O:9])=[N:21][C:22]=3[CH:23]=2)[C:15]([CH3:34])([CH3:33])[C:14]1=[O:35]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13343780HCID 13343780, compound

Product 1

HCID 13343782HCID 13343782, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

31 ml of a 10% solution of m-chloroperbenzoic acid in ethyl acetate were added dropwise with intensive stirring at 0°-5° C. to 6.16 g of 5,7-dihydro-5,5,7,7-tetramethyl-2-[(2-pyridylmethyl)thio]indeno(5,6-d)-imidazol-6(1H)-one, dissolved in 100 ml of methylene chloride, in a 250 ml sulfonation flask equipped with stirrer, thermometer, dropping funnel and calcium chloride tube. 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 ml of 2N soda, then neutral with water, dried over sodium sulfate and evaporated in vacuo. Crystallization of the residue from acetonitrile gave 2.7 g (42.3% of theory) of 5,7-dihydro-5,5,7,7-tetramethyl-2-[(2-pyridylmethyl)sulfinyl]indeno(5,6-d)imidazol-6(1H)-one of melting point 201°-203° C.

Workup

  1. customequipped with stirrer
  2. washwas washed twice with 250 ml of 2N soda
  3. dry with materialneutral with water, dried over sodium sulfate
  4. customevaporated in vacuo
  5. customCrystallization of the residue from acetonitrile

Sources & evidence

ORD record
ord-01ebf6433c5d4ba788a9adedda94ec9f
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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