2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

HRID 2165076Notes

Reaction equation

HRID 2165076 reaction equation
[NH2:1][C:2]1[C:3]([SH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:9][CH2:10][C:11](OCC)(OCC)OCC>C(O)C>[Cl:9][CH2:10][C:11]1[S:8][C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[CH:5][N:4]=2

Participants

4

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 178418545HCID 178418545, compound

Product 1

HCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Chloromethyl-thiazolo[5,4-b]pyridine was prepared similarly by heating a mixture of 3-amino-2-mercaptopyridine (3.6 g), 2-chloro-1,1,1-triethoxyethane (6.5 g) and ethanol (60 ml) at 60° C. for 4 hours. The crude solid resulting from evaporation of ethanol was chromatographed over silica gel to obtain 2.94 g of the product, m.p. 71°-73° C.

Workup

  1. temperatureby heating
  2. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-8257dd66022b45e3bcf2f16c656c4d6b
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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