m-Chloroperbenzoic acid → HCID 20464689, compound

HRID 223463Notes

Reaction equation

HRID 223463 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([S:33][CH2:34][CH:35]3[O:39][CH2:38][CH2:37][O:36]3)[NH:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]2[N:23]=[C:22]([S:33]([CH2:34][CH:35]3[O:39][CH2:38][CH2:37][O:36]3)=[O:9])[NH:21][C:20]=2[C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20464696HCID 20464696, compound

Product 1

HCID 20464689HCID 20464689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.19 g (80%) of 3-chloroperbenzoic acid in 100 ml. of dichloromethane is added dropwise to a solution of 1.99 g. of [4,5-bis(4-methoxyphenyl)-2-imidazolyl]-(1,3-dioxolan-2-ylmethyl)sulfide in 150 ml. of dichloromethane. The mixture is stirred for 4 hours at room temperature, then washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated under vacuum. The residue is crystallized from ethyl acetate/hexane. After recrystallization from ethyl acetate/hexane, 1.43 g. of [4,5-bis(4-methoxyphenyl)-2-imidazolyl]-(1,3-dioxolan-2-ylmethyl)sulfoxide is obtained, m.p. 203°-204°.

Workup

  1. washwashed with sodium bicarbonate solution
  2. dry with materialthe organic solution is dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue is crystallized from ethyl acetate/hexane
  5. customAfter recrystallization from ethyl acetate/hexane, 1.43 g

Sources & evidence

ORD record
ord-40c41f79a97c4638a39fe4013bc92b98
Source dataset
uspto-grants-1982_10
Patent number
US04355039

Reaction notes

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