m-Chloroperbenzoic acid → HCID 13343782, compound

HRID 1903145Notes

Reaction equation

HRID 1903145 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 6.1 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 2 N 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 2 N 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-2aed77ef97f54626aa3a324130e90227
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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