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

HRID 1372672Notes

Reaction equation

HRID 1372672 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F: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]([F: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 114923512-Bromo-6-fluoro-1,3-benzothiazoleHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 58778884Methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetateYield 32%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (8 ml), 2-bromo-6-fluorobenzothiazole (330 mg, 1.42 mmol), methyl 4-amino-3-chlorophenylacetate (284 mg, 1.42 mmol), and pyridinium p-toluenesulfonate (PPTS) (107 mg, 0.43 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-fluoro-2-benzothiazolyl)aminophenyl)acetate (158 mg, 32%) 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-9b67edc1d1dd499282714d68c8e50910
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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