4-Bromoaniline → HCID 7147097, compound

HRID 432432Notes

Reaction equation

HRID 432432 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[S:11][C:12]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:13]=2[N:14]=1>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[S:11][C:12]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 771762,6-Dichlorobenzothiazole

Product 1

HCID 7147097HCID 7147097, compoundYield 100%

Procedure

Solid 4-Bromoaniline (1.00 g, 5.81 mmol) and 2,6-dichlorobenzothiazole (1.18 g, 5.81 mmol) were heated at 140° C. for 3 days in a flask equipped with an air condenser (fusion occurred within a few minutes to give a clear liquid which solidified over the course of 3 days). The reaction mixture was allowed to cooled to ambient temperature to give N-(4-bromophenyl)-N-(6-chloro-1,3-benzothiazol-2-yl)amine (1.97 g, 5.81 mmol): RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 14.65 min.

Workup

  1. customequipped with an air condenser (fusion
  2. waitoccurred within a few minutes
  3. customto give a clear liquid which
  4. customsolidified over the course of 3 days

Sources & evidence

ORD record
ord-e0aa41269f7d4554b3fb1ebd83e5bd28
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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