Dimethyl Sulfoxide → Ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetate

HRID 1590269Notes

Reaction equation

HRID 1590269 reaction equation
[OH:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5].IC.[C:36](=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)C>[CH3:36][O:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate

Product 1

HCID 6005279Ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetateYield 74.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To ethyl (Z)-2-(hydroxyimino)-2-[2-(triphenylmethyl)aminothiazol-4-yl]acetate(46 g) were added iodo methane(28.4 g), potassium carbonate (27.6 g) and dimethylsulfoxide(500 ml), and the mixture was stirred for 5 hours at room temperature. After ethyl ether(2 l) was added to the reaction mixture, the mixture was washed 5 times with distilled water(500 ml). The separated organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and then concentrated. The residue was chromatographed over silica gel to give the above-indicated compound (35.2 g) as a pale yellow solid.

Workup

  1. washthe mixture was washed 5 times with distilled water(500 ml)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-7146b1e6e2424b97b3829685580fd312
Source dataset
uspto-grants-1993_04
Patent number
US05202315

Reaction notes

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