Sulfuric Acid → 2-Methyl-5H-thiazolo[4,5-c]pyridin-4-one

HRID 1443113Notes

Reaction equation

HRID 1443113 reaction equation
CO[CH:3](OC)[CH2:4][C:5]1[S:9][C:8]([CH3:10])=[N:7][C:6]=1[C:11]([NH2:13])=[O:12].S(=O)(=O)(O)O>O1CCOCC1>[CH3:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][NH:13][C:11](=[O:12])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 685435945-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carboxylic acid amide

Product 1

HCID 685409792-Methyl-5H-thiazolo[4,5-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carboxylic acid amide (1.0 g, 4.3 mmol) was dissolved in 35 ml dioxane and 0.3 ml conc. sulfuric acid was added. The reaction mixture was stirred for 2 hrs at room temperature. The white suspension was cooled to 0° C. and stirred for 10 min. The suspension was filtered and washed with cold dioxane. The solid was dried for 1 hour at 50° C. and <30 mbar. The desired product was obtained as a white solid (0.7 g, 97%), MS: m/e=167.1 (M+H+).

Workup

  1. temperatureThe white suspension was cooled to 0° C.
  2. stirringstirred for 10 min
  3. filtrationThe suspension was filtered
  4. washwashed with cold dioxane
  5. customThe solid was dried for 1 hour at 50° C.

Sources & evidence

ORD record
ord-e58b557f445641a5bcadbf9ac74a1430
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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