HCID 13344846, compound → HCID 20271324, compound

HRID 485046Notes

Reaction equation

HRID 485046 reaction equation
[CH3:1][N:2]([CH2:10][C:11]#[CH:12])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]([CH2:10][C:11]#[CH:12])[C:3]1[S:4][CH:5]=[C:6]([CH:8]=[O:9])[N:7]=1

Participants

4

Reactant 1

HCID 13344846HCID 13344846, compound

Product 1

HCID 20271324HCID 20271324, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(N-Methyl-2-propynylamino)-4-hydroxymethylthiazole (i) (4.36 g) was dissolved in methylene chloride (20 ml) and manganese dioxide (10 g) was added thereto. The mixture was stirred at room temperature for 16 hours and filtered off. The filtrate was evaporated and the residue was applied to column chromatography on silica gel (50 g) to give 2-(N-methyl-2-propynylamino)-4-formylthiazole (j) (2.56 g, yield 59%) from chloroform-ether (3:1) eluate as an oil.

Workup

  1. filtrationfiltered off
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c0aff894581e42c392197d507f3ccd35
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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