Acetic Acid → 4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amine

HRID 249298Notes

Reaction equation

HRID 249298 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][NH2:9])[N:6]=1.[C:10](O)(=O)C.C=O>CO>[NH2:1][C:2]1[S:3][C:4]2[CH2:10][NH:9][CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 109646314-(2-Aminoethyl)-1,3-thiazol-2-amine

Product 1

HCID 135196874H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-4-(2-aminoethyl)thiazole (1.57 g, 11.0 mmol) in methanol (120 ml) was treated with acetic acid (0.15 ml, 2.6 mmol) and formaldehyde (0.89 ml of a 37% aqueous solution, 11 mmol). After ten minutes, the reaction mixture was concentrated in vacuo and subjected to column chromatography (eluant: 95:4:1 chloroform:methanol:concentrated ammonium hydroxide). The product was obtained as a white solid, m.p. 169°-173° (1.547 g, 10.0 mmol, 91% yield).

Workup

  1. waitAfter ten minutes
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe product was obtained as a white solid, m.p. 169°-173° (1.547 g, 10.0 mmol, 91% yield)

Sources & evidence

ORD record
ord-d5e6ae95a55e4e22919bb626a738542d
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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