Water → Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate

HRID 13532

Reaction equation

HRID 13532 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1)=[O:2].[Cl:16]N1C(=O)CCC1=O.O>CN(C=O)C>[CH:1]([NH:3][C:4]1[S:5][C:6]([Cl:16])=[C:7]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 2733245Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetate

Product 1

HCID 14326717Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(Formylaminothiazol-4-yl)-2-oxoacetate (9.1 g, 39.87 mmol) (obtained from Aldrich, Milwaukee, Wis.) was slurried in 50 mL of anhydrous DMF. N-Chlorosuccinimide (5.6 g, 41.86 mmol) was added as a solid and the suspension was stirred at room temperature. After 18 hours, the reaction mixture was poured into 500 mL of water. The resulting white precipitate was filtered, washed with water and air dried to afford the title intermediate as a white solid.

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-572aaac4a1614a098cd42dd318d131d2
Source dataset
uspto-grants-2010_06
Patent number
US07728127B2

Linked notes

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