Hydrochloric Acid → HCID 20144978, compound

HRID 1906012Notes

Reaction equation

HRID 1906012 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:6]([C:8](OCC)=[O:9])[N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH:8]([C:6]1[N:7]=[C:3]([NH:2][CH3:1])[S:4][C:5]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20145031HCID 20145031, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20144978HCID 20144978, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methylamino-5-(4-pyridyl)-4-thiazolecarboxylate (2.6 g) in dry tetrahydrofuran (120 ml) was added lithium aluminum hydride (0.38 g) at -10° C. with stirring, which was continued at -10~-3° C. for 30 minutes. The reaction mixture was poured into ice-water and the resultant solution was acidified to pH 1.0 with 10% hydrochloric acid. The insoluble material was filtered off. The filtrate was adjusted to pH 7.0 with 20% aqueous solution of potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic extract was concentrated in vacuo. The precipitate was collected by filtration, washed with ethyl acetate and dried in vacuo to give 4-formyl-2-methylamino-5-(4-pyridyl)thiazole (0.8 g). mp 243°-245° C. (dec.)

Workup

  1. filtrationThe insoluble material was filtered off
  2. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-724c1cd954f54db78e2ba1eb41ee1c43
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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