Acetic Anhydride → 5-Bezyloxy-3-acetoxymethythio-1,2,4-thiadiazole

HRID 917342Notes

Reaction equation

HRID 917342 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)C.N1C(C)=CC=CC=1C.[CH2:16]([O:23][C:24]1[S:28][N:27]=[C:26]([S:29](C)=O)[N:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>>[CH2:16]([O:23][C:24]1[S:28][N:27]=[C:26]([S:29][CH2:1][O:4][C:5](=[O:7])[CH3:6])[N:25]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 516892Sodium BicarbonateHCID 230324475-Benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole

Product 1

HCID 589628945-Bezyloxy-3-acetoxymethythio-1,2,4-thiadiazoleYield 64.5%

Procedure

Into 1.5 g of acetic anhydride were added 620 mg of 2,6-lutidine and 500 mg of 5-benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole under ice-cooling. After stirring for 15 hours at room temperature, the reaction mixture was added to saturated sodium hydrogen carbonate aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 376 mg of 5-bezyloxy-3-acetoxymethythio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (44)).

Workup

  1. temperaturecooling
  2. extractionextracted with t-butyl methyl ether
  3. concentrationThe organic layer was concentrated
  4. customthe residue obtained

Sources & evidence

ORD record
ord-54c407c5d82d447f93314033ab40fc69
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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