Dichloromethane → 2-Chlorothiazolo[4,5-b]pyrazine

HRID 1947451Notes

Reaction equation

HRID 1947451 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[NH:3][C:2]1=S.C(Cl)[Cl:12].S(Cl)(Cl)(=O)=O.[OH-].[Na+]>O>[Cl:12][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][N:8]=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 13772324[1,3]Thiazolo[4,5-b]pyrazine-2(3H)-thione

Product 1

HCID 574827642-Chlorothiazolo[4,5-b]pyrazineYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3H-thiazolo[4,5-b]pyrazine-2-thione (4.36 g, 25.8 mmol) and DCM (60 mL) was sonicated (5 min). The suspension was treated with sulfuryl chloride (99.9 g, 740 mmol, 60 mL) and heated (40° C., 16 h). The reaction mixture was cooled (0° C.) and slowly treated with H2O (250 mL), followed by 4 N NaOH (550 mL). The aqueous mixture was extracted with EtOAc (2×1800 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a solid (2.63 g, 53%). MS (ESI): mass calculated for C5H2ClN3S, 170.9; m/z found, 172.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.84 (d, J=2.5, 1H), 8.75 (d, J=2.5, 1H).

Workup

  1. customwas sonicated (5 min)
  2. temperatureThe reaction mixture was cooled (0° C.)
  3. extractionThe aqueous mixture was extracted with EtOAc (2×1800 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c3a96e95f924d329239787700849c73
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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