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

HRID 1992693Notes

Reaction equation

HRID 1992693 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-6a8710741cc6490cbc1031c4c66d2079
Source dataset
uspto-grants-2010_01
Patent number
US07649080B2

Reaction notes

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