Selenium Dioxide → Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate

HRID 463852

Reaction equation

HRID 463852 reaction equation
[Se](=O)=O.[O:4]1CCOCC1.[S:10]([NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1)([CH3:13])(=[O:12])=[O:11]>O>[S:10]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[O:4])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1)([CH3:13])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 3145078Ethyl 2-methanesulfonamidothiazol-4-ylacetate

Product 1

HCID 19978726Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of selenium dioxide (11.1 g.), dioxane (250 ml.) and water (5 ml.) was stirred for 15 minutes at 110° to 115° C. to give yellow solution. Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)acetate (26.4 g) was added thereto with stirring at the same temperature. After stirring for 1 hour, the reaction mixture was decanted with heating and cooled to precipitate yellow crystals. The crystals were collected by filtration, washed with dioxane and ether and dried to give ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate (23.5 g.).

Workup

  1. customto give yellow solution
  2. stirringwith stirring at the same temperature
  3. stirringAfter stirring for 1 hour
  4. customthe reaction mixture was decanted
  5. temperaturewith heating
  6. temperaturecooled
  7. customto precipitate yellow crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed with dioxane and ether
  10. customdried

Sources & evidence

ORD record
ord-d1da65eadd1c4c1196592e17b12e83d8
Source dataset
uspto-grants-1985_10
Patent number
US04544653

Linked notes

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