2-Bromo-4-chlorobenzothiazole → HCID 58778599, compound

HRID 1372678Notes

Reaction equation

HRID 1372678 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[Cl:24].[NH+]1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:11][C:7]1[C:5]2[N:6]=[C:2]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=3[Cl:24])[S:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 771782-Bromo-4-chlorobenzothiazoleHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetateHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 58778599HCID 58778599, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (7 ml), 2-bromo-4-chlorobenzothiazole (647 mg, 2.60 mmol), methyl 4-amino-3-chlorophenylacetate (520 mg, 2.60 mmol), and pyridinium•p-toluenesulfonate (PPTS) (200 mg, 0.80 mmol) were heated under reflux for 7 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1, v/v) eluate fractions, methyl (4-(4-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetate (556 mg, 58%) was obtained as a yellow amorphous substance.

Workup

  1. temperatureunder reflux for 7 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1

Sources & evidence

ORD record
ord-8b7e2bf5b4fc446d9ef604a3fd736b30
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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