Water → HCID 3394160, compound

HRID 1714724Notes

Reaction equation

HRID 1714724 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1.N1C=CC=CC=1.O>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 3394160HCID 3394160, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.07 g of o-chlorobenzoyl chloride was added to a solution in which 1.00 g of ethyl 2-amino-1,3-thiazole-4-carboxylate and 0.69 g of pyridine were dissolved in THF, under ice cooling. Then, after the reaction mixture was stirred at room temperature for 1 hr, it was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous 2N-hydrochloric acid solution and dried on anhydrous magnesium sulfate. After distilling off the solvent, the crude product obtained was washed with a mixed solvent of hexane and t-butyl methyl ether to obtain 1.52 g of the aimed ethyl 2-(2-chlorobenzoyl)amino-1,3-thiazole-4-carboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 2N-hydrochloric acid solution
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crude product obtained
  6. washwas washed with a mixed solvent of hexane and t-butyl methyl ether

Sources & evidence

ORD record
ord-8b5de3d0307e4bafa61d76e9d278d270
Source dataset
uspto-grants-2010_09
Patent number
US07799738B2

Reaction notes

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