Lithium Chloride → HCID 18916379, compound

HRID 1290632Notes

Reaction equation

HRID 1290632 reaction equation
[NH2:1][C:2]1[C:10]2[S:9][C:8](Cl)=[N:7][C:6]=2[C:5]([Cl:12])=[CH:4][CH:3]=1.[CH3:13][S-:14].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Li+]>CN(C)C=O>[NH2:1][C:2]1[C:10]2[S:9][C:8]([S:14][CH3:13])=[N:7][C:6]=2[C:5]([Cl:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 4378561Sodium methanethiolateHCID 12479787HCID 12479787, compound

Product 1

HCID 18916379HCID 18916379, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The reaction was repeated with 2.3 grams (10.5 mmole) of 7-amino-2,4-dichlorobenzothiazole, 1.2 grams (17 mmole) of sodium thiomethoxide, and 25 mL of N,N-dimethylformamide as reagents. After the reaction mixture had been heated for two hours at 60° C. the 0.8 grams from the previous reaction was added, and the reaction mixture was heated for an additional three hours. The reaction mixture was cooled and poured into 300 mL of cold aqueous sodium bicarbonate solution. To this was then added 10 grams of solid lithium chloride. The reaction mixture was extracted with three 100 mL portions of diethyl ether. The combined organic extracts were washed with an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding 2.0 grams of 7-amino-2-methylthio-4-chlorobenzothiazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customfrom the previous reaction
  2. additionwas added
  3. temperaturethe reaction mixture was heated for an additional three hours
  4. temperatureThe reaction mixture was cooled
  5. extractionThe reaction mixture was extracted with three 100 mL portions of diethyl ether
  6. washThe combined organic extracts were washed with an aqueous saturated sodium chloride solution
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83caf3e745d14aa9a4f4d7b409430e74
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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