Hydrochloric Acid → HCID 67916362, compound

HRID 1534298Notes

Reaction equation

HRID 1534298 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:10]1[CH:55]=[CH:54][C:13]([CH2:14][C:15]2[C:24]3[C:23]([CH3:26])([CH3:25])[CH2:22][CH2:21][C:20]([CH3:28])([CH3:27])[C:19]=3[CH:18]=[CH:17][C:16]=2[S:29][C:30]2[CH:39]=[CH:38][C:37]3[C:36]([CH3:41])([CH3:40])[CH2:35][CH2:34][C:33]([CH3:43])([CH3:42])[C:32]=3[C:31]=2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([OH:53])=[O:52])=[CH:47][CH:46]=2)=[CH:12][CH:11]=1)([OH:9])=[O:8].Cl>O.C(O)C.CN(C)C=O>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C:15]2[C:24]3[C:23]([CH3:25])([CH3:26])[CH2:22][CH2:21][C:20]([CH3:27])([CH3:28])[C:19]=3[CH:18]=[CH:17][C:16]=2[S:29]([C:30]2[CH:39]=[CH:38][C:37]3[C:36]([CH3:41])([CH3:40])[CH2:35][CH2:34][C:33]([CH3:42])([CH3:43])[C:32]=3[C:31]=2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([OH:53])=[O:52])=[CH:47][CH:46]=2)=[O:2])=[CH:54][CH:55]=1)([OH:9])=[O:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 67916399HCID 67916399, compound

Product 1

HCID 67916362HCID 67916362, compoundYield 21.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.4 g (16 mmol) of sodium periodate in 30 ml of water was added dropwise to 5.3 g (15 mmol) of the thioether from Example 10 in a mixture of 150 ml of ethanol and 40 ml of dimethylformamide at 0° C., and the mixture was then stirred at the same temperature for 2 hours and at room temperature overnight. The reaction solution was then poured into water, the pH was adjusted to 5 with 2N hydrochloric acid, the mixture was extracted with dichloromethane, and the organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. Crystallization of the oily residue from ethanol yielded 2.2 g of title compound of melting point 198°-200° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customCrystallization of the oily residue from ethanol

Sources & evidence

ORD record
ord-8b936192a60b4a35af13b65b09eb33d7
Source dataset
uspto-grants-1992_02
Patent number
US05087743

Reaction notes

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