Hydrochloric Acid → HCID 7147097, compound

HRID 2356798Notes

Reaction equation

HRID 2356798 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.O1CCOCC1>C(O)CCC>[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 4

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 312751,4-DioxaneHCID 771762,6-Dichlorobenzothiazole

Product 1

HCID 7147097HCID 7147097, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2,6-dichlorobenzothiazole (0.71 g, 3.5 mmol) and 4-bromoaniline (0.61 g, 3.5 mmol) in n-butanol (6 mL) was heated at 60-70° C. under nitrogen to obtain a solution, to which 4 M HCl in dioxane (0.43 mL, 1.73 mmol) was then slowly added dropwise. The reaction mixture was then heated at 90° C. for 18 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The resulting solid was triturated with ethanol and collected by filtration. This yielded 1.09 g (93%) of the title compound. LC/MS m/z 339 (MH+); retention time 3.98 min. 1H NMR (CD3OD) δ 7.31 (d, 1H), 7.42-7.58 (m, 5H), 7.61 (d, 1H).

Workup

  1. customto obtain a solution
  2. temperatureThe reaction mixture was then heated at 90° C. for 18 h
  3. temperatureUpon cooling to rt
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe resulting solid was triturated with ethanol
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ca305b51c29f466bb36291b0d4ac80aa
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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