1-Bromo-2-Chloroethane → HCID 67737284, compound

HRID 326244Notes

Reaction equation

HRID 326244 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][NH:13][CH3:14])=[CH:10][C:5]=2[S:4](=[O:15])[CH2:3]1.[Cl:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]([CH3:14])[CH2:18][CH2:17][Cl:16])=[CH:10][C:5]=2[S:4](=[O:15])[CH2:3]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 67713193HCID 67713193, compound

Product 1

HCID 67737284HCID 67737284, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

In a ground-necked flask, 6 mmol of 3-methyl-6-(2-(N-methylamino)ethyl]benzothiazolinone are dissolved in 50 ml of dioxane, 20 mmol of 1-chloro-2-bromoethane and 20 mmol of potassium carbonate. The mixture is stirred for 48 hours at a temperature of 60° C. After cooling, the mixture is evaporated and the reaction medium is extracted with chloroform after adding water. After washing, drying and evaporation of the organic phase, 3 -methyl-6-{2-[N-methyl-N-(2-chloroethyl) amino]ethyl}benzothiazolinone is obtained, which product is transferred to a ground-necked flask. A catalytic amount of potassium iodide, 25 cm3 of methanol and 10 cm3 of chloroform are added. A stream of gaseous ammonia is bubbled into the solution to the point of saturation and a reflux condenser is then fitted. The temperature is stabilized at 50° C. with an oil bath and the mixture is then left stirring magnetically for 72 hours. After cooling, the reaction mixture is evaporated on a water bath under vacuum. The residue is ground with distilled water acidified with 5% HCl solution, and then drained. The filtrate is recovered, washed with ethyl acetate and then alkalinized with 10% sodium hydroxide solution. It is extracted with chloroform, leaving the 2 phases agitating for 1/2 hour, and the organic phase is washed with distilled water and then dried over calcium chloride. The organic phase is evaporated on a water bath under vacuum, the residue is then taken up in absolute ethanol, a stream of gaseous HCl is bubbled through and the mixture is then evaporated to dryness on a water bath under vacuum. The product is dried and then recrystallized.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is evaporated
  3. extractionthe reaction medium is extracted with chloroform
  4. additionafter adding water
  5. washAfter washing
  6. customdrying
  7. customevaporation of the organic phase

Sources & evidence

ORD record
ord-7b0d5c52471f4ad68569567294d327aa
Source dataset
uspto-grants-1993_12
Patent number
US05268381

Reaction notes

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