Hydrochloric Acid → HCID 178527801, compound

HRID 707273Notes

Reaction equation

HRID 707273 reaction equation
[NH2:1][C:2]1[C:3](Br)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O[C:12]([S-:14])=[S:13])C.[K+].CN(C)C=O.Cl>O>[N:1]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[S:13][C:12]=1[SH:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6428163-Amino-2-bromopyridineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178527801HCID 178527801, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

In a round-bottomed flask, 3-amino-2-bromopyridine (1.14 g, 6.59 mmol), potassium ethylxanthate (2.32 g, 14.5 mmol) and dry dimethylformamide (4 mL) were mixed. The reaction mixture was heated to 130° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (150 mL). 5 N Hydrochloric acid (4 mL) was added and the mixture was stirred for 10 minutes. The precipitate formed was collected by filtration and dried in a vacuum oven at 80° C. overnight to give thiazolo[5,4-b]pyridine-2-thiol (1.07 g, 6.36 mmol, 97% yield) as tan solid. 1H NMR (300 MHz, DMSO-d) δ ppm 7.43 (dd, J=8.18, 4.82 Hz, 1 H) 7.63 (dd, J=8.18, 1.32 Hz, 1 H) 8.34-8.47 (m, 1 H). ESI (M+1) 168.9.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. customdried in a vacuum oven at 80° C. overnight

Sources & evidence

ORD record
ord-b7a70cf253534b25a42188c03b8bc60e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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