m-Chloroperbenzoic acid → HCID 13343782, compound

HRID 745571Notes

Reaction equation

HRID 745571 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-72ca7adefc304f3db04df55496d069c5
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

Loading…