Hydrochloric Acid → HCID 20454634, compound

HRID 1462109Notes

Reaction equation

HRID 1462109 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:36]=[CH:35][C:16]([CH2:17][S:18][CH:19]([S:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:15][CH:14]=1.CCOCC.Cl>C(Cl)(Cl)Cl>[ClH:1].[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][S:18]([CH:19]([S:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[O:9])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 13320331HCID 13320331, compound

Product 1

HCID 20454634HCID 20454634, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 85% m-chloroperbenzoic acid (1.66 g, 9.63 mmoles) in chloroform (80 ml) was added dropwise during 1 hour to a stirred, cooled (ice/water) solution of 1-[2,2-bis(4-methylbenzylthio)ethyl]-1H-imidazole (3.55 g, 9.63 mmoles) in chloroform (125 ml). The solution was stirred for 18 hours at ambient temperature and then washed successively with aqueous Na2CO3 (2×), H2O and brine. The solution was dried over Na2SO4 and concentrated to leave a mixture of the diastereoisomeric mono-sulfoxides as a cloudy oil. Trituration of the oil with ether afforded the free base of diastereomer A (1.45 g), mp 86°-92° which was converted into the hydrochloride salt, mp 167°-170° with ethereal hydrogen chloride. Hydrogen chloride was bubbled into the ethereal mother liquor from the trituration step to give a mixture of the hydrochloride salts which after recrystallization from acetonitrile provided additional diastereomer A, mp 164°-168° (0.42 g) and 0.57 g of diastereomer B, mp 141°-146°.

Workup

  1. washwashed successively with aqueous Na2CO3 (2×), H2O and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customto leave
  5. customHydrogen chloride was bubbled into the ethereal mother liquor from the trituration step
  6. customto give
  7. customafter recrystallization from acetonitrile provided additional diastereomer A, mp 164°-168° (0.42 g) and 0.57 g of diastereomer B, mp 141°-146°

Sources & evidence

ORD record
ord-e4d11fb9450245d49b7c2c18acff9972
Source dataset
uspto-grants-1984_07
Patent number
US04458079

Reaction notes

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