Potassium Carbonate → HCID 20145030, compound

HRID 648569Notes

Reaction equation

HRID 648569 reaction equation
S(Cl)(Cl)(=O)=O.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:21])[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=1.[NH2:22][C:23]([NH2:25])=[S:24].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O1CCCC1.O>[NH2:25][C:23]1[S:24][C:13]([C:12](=[O:21])[C:8]2[CH:9]=[CH:10][CH:11]=[N:6][CH:7]=2)=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:22]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 2723790ThioureaHCID 12246594Ethyl α,γ-dioxo-3-pyridinebutanoate

Product 1

HCID 20145030HCID 20145030, compoundYield 16.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of sulfuryl chloride (2.84 g) in methylene chloride (5 ml) was dropwise added to a solution of ethyl 4-(3-pyridyl)-2,4-dioxo-butyrate (4.42 g) in methylene chloride (40 ml) at 18° C. to 30° C. After being stirred at ambient temperature for one hour, the mixture was added to a solution of thiourea (4.56 g) in a mixture of tetrahydrofuran (50 ml) and water (10 ml). The resulting mixture was adjusted to pH 7.5 with 20% aqueous potassium carbonate and stirred for one hour, and then the solvent was removed in vacuo. To the residue was added a mixture of water and ethyl acetate, and the mixture was acidified to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 9.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give ethyl 2-amino-5-nicotinoyl-4-thiazolecarboxylate (0.9 g). mp 221° C. (dec.).

Workup

  1. stirringstirred for one hour
  2. customthe solvent was removed in vacuo
  3. additionTo the residue was added
  4. additiona mixture of water and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-2921aed18cb242f0a16350c64ab0eecf
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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