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

HRID 638423Notes

Reaction equation

HRID 638423 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].C>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

7

Reactant 5

HCID 297MethaneHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 3145078Ethyl 2-methanesulfonamidothiazol-4-ylacetateHCID 178470766HCID 178470766, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution prepared by stirring a mixture of selenium dioxide (0.22 g.), dioxane (10 ml.) and water (0.2 ml.) for 10 minutes at 110° C. was added ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (0.53 g.), and the mixture was refluxed for 1 hour. After the reaction, the reaction mixture was treated with activated charcoal. The precipitated crystals in the filtrate were collected by filtration and dried to give white crystals of ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (0.22 g.), mp. 222° to 225° C. On the other hand, the remaining filtrate was concentrated and the residue was washed with water and diethyl ether in turn and then dried to give the same object compound (0.12 g.)

Workup

  1. customTo a solution prepared
  2. temperaturethe mixture was refluxed for 1 hour
  3. customAfter the reaction
  4. filtrationThe precipitated crystals in the filtrate were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-5158e908642240ee91eeb08b7d57b8be
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

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