Hydrochloric Acid → HCID 53728888, compound

HRID 1906013Notes

Reaction equation

HRID 1906013 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=O)[N:7]=1.[OH2:16].Cl.[O:18]1[CH2:22]C[CH2:20][CH2:19]1>>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=[CH:20][C:19]([O:18][CH3:22])=[O:16])[N:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 20144978HCID 20144978, compound

Product 1

HCID 53728888HCID 53728888, compound

Procedure

A mixture of 2-methylamino-4-formyl-5-(4-pyridyl)thiazole (1.1 g) and triphenylphosphinecarbomethoxymethylene (3.34 g) in tetrahydrofuran (80 ml) was stirred at 40° to 45° C. for 2.5 hours. The reaction mixture was poured into water and the resultant solution was acidified to pH 1.0 with 10% hydrochloric acid. The acidified solution was washed with ethyl acetate. The aqueous solution was adjusted to pH 7.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (8:2). The fractions containing the desired compound were combined and evaporated in vacuo to give methyl 2-methylamino-5-(4-pyridyl)-4-thiazoleacrylate (trans isomer) (0.66 g). mp 166°-167° C.

Workup

  1. washThe acidified solution was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. additionthe residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (8:2)
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c344388b3e6f42fb858f8a96c56772b4
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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