Hydrochloric Acid → HCID 820106, compound

HRID 1419717Notes

Reaction equation

HRID 1419717 reaction equation
C[Mg]Cl.Br[C:5]1[S:6][C:7]2[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:8]=2[N:9]=1.Cl>O1CCCC1>[Cl:15][C:10]1[C:8]2[N:9]=[CH:5][S:6][C:7]=2[CH:13]=[C:12]([Cl:14])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 53966919HCID 53966919, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 820106HCID 820106, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 98 mmol of methyl magnesium chloride in tetrahydrofruan was added dropwise to a solution of 14 g (49 mmol) of 2-bromo-4,6-dichlorobenzothiazole in 200 ml of tetrahydrofuran, which solution had been cooled to -78° C. After 2 hours, acidification was effected with 10% strength hydrochloric acid and the product was then extracted with diethyl ether. The organic phase was washed with water, saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate and finally evaporated down. Purification of the crude product was effected by means of silica gel chromatography (eluent: 5:1 petroleum ether/methyl tert-butyl ether). Yield: 5.2 g.

Workup

  1. extractionthe product was then extracted with diethyl ether
  2. washThe organic phase was washed with water, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customfinally evaporated down
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-0256e4b1e6f246f5bc48ea661471878d
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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