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

HRID 2234731Notes

Reaction equation

HRID 2234731 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-5d77def39f4d4e0aa75453ec99f14523
Source dataset
uspto-grants-2010_05
Patent number
US07713931B2

Reaction notes

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