HCID 54042463, compound → HCID 14931751, compound

HRID 1252063Notes

Reaction equation

HRID 1252063 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=[O:13])[N:9]=1)(=[O:3])[CH3:2].[H][H]>CN(C)C=O.[Pd]>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[O:13])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54042463HCID 54042463, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14931751HCID 14931751, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-acetylamino-4-(2-formylvinyl)thiazole (2.24 g) in N,N-dimethylformamide was added 10% palladium on carbon (11.2 g) and hydrogen gas was bubbled thereinto for 4.5 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V) to give 2-acetylamino-4-(2-formylethyl)thiazole (2.06 g).

Workup

  1. customwas bubbled
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V)

Sources & evidence

ORD record
ord-73f680c9d8094e89b8a83dfba7cdfd5c
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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