Water → HCID 178527792, compound

HRID 1845898Notes

Reaction equation

HRID 1845898 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.C(O[C:13](=[S:15])[S-:14])C.[K+].CN1C(=O)CCC1.O>C(O)(=O)C>[Cl:9][C:4]1[N:3]=[C:2]2[S:14][C:13]([SH:15])=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 1128462,6-Dichloro-3-pyridylamineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178527792HCID 178527792, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

To a round bottom flask was added 2,6-dichloropyridin-3-amine (21.4 g, 131 mmol), potassium ethoxy(thioxo)methanethiolate (42.1 g, 262 mmol), and anhydrous NMP (300 mL). The reaction mixture was then heated to 170° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 3.5 hours. The crude reaction mixture was then allowed to cool to room temperature, and acidified to pH 5 with glacial acetic acid, which led to a precipitate which was collected by filtration. This precipitate was then suspended in ethyl acetate and washed with water, then brine, dried over sodium sulfate, filtered, and concentrated to give 5-chloro[1,3]thiazolo[5,4-b]pyridine-2-thiol (1-1) as a tan solid. HRMS (M+H)+: observed=202.9502, calculated=202.9499.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe crude reaction mixture
  4. temperatureto cool to room temperature
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dc619bbc02914eaf85ede419ee8ff357
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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