Hydrochloric Acid → HCID 7147097, compound

HRID 1944106Notes

Reaction equation

HRID 1944106 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.Cl>CCO.O1CCOCC1>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[S:3][C:4]3[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 771762,6-Dichlorobenzothiazole

Product 1

HCID 7147097HCID 7147097, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of 2,6-dichlorobenzothiazole (2.52 g, 12.3 mmol) and 4-bromoaniline (2.12 g, 12.2 mmol) in EtOH (15 mL) was added 4 N HCl in dioxane (0.2 mL, 0.8 mmol). The reaction mixture was stirred at 140° C. in a microwave reactor for 1 h. After cooling to room temperature, the resulting suspension was filtered. The collected solid was washed with MeOH (10 mL), and dried in a 50° C. vacuum oven for 16 h to afford 3.28 g (80%) of the title compound as a white solid. HPLC/MS (method C): retention time=4.24 min, [M+H]+=339.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting suspension was filtered
  3. washThe collected solid was washed with MeOH (10 mL)
  4. customdried in a 50° C. vacuum oven for 16 h

Sources & evidence

ORD record
ord-bc76a02f199d4a23933e40b4c30ca411
Source dataset
uspto-grants-2013_03
Patent number
US08394823B2

Reaction notes

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