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

HRID 1659388Notes

Reaction equation

HRID 1659388 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-88305e97fbe64e2eaec7bc1c4cbf55fb
Source dataset
uspto-grants-1981_12
Patent number
US04303655

Reaction notes

Loading…