Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate

HRID 1372674

Reaction equation

HRID 1372674 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][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].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 117084142-bromo-6-methylbenzo[d]thiazoleHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 58778443Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetateYield 26%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (10 ml), 2-bromo-6-methylbenzothiazole (703 mg, 3.08 mmol), methyl 4-amino-3-chlorophenylacetate (615 mg, 3.08 mmol), and pyridinium p-toluenesulfonate (PPTS) (232 mg, 0.92 mmol) were heated under reflux for 10 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 (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate (274 mg, 26%) was obtained as a pale yellow solid.

Workup

  1. temperatureunder reflux for 10 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-5ed36a50cb3947d499c75b1a568ec65e
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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