HCID 86589713, compound → HCID 18506137, compound

HRID 1357388Notes

Reaction equation

HRID 1357388 reaction equation
CC(C)(C)C[O:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]([NH:21][C:22](=[O:32])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:33])=[CH:10][CH:9]=1)(=[O:7])=[O:6]>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C>[Cl:33][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:15]=1[O:14][C:11]1[CH:10]=[CH:9][C:8]([S:5]([OH:7])(=[O:6])=[O:4])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 86589713HCID 86589713, compound

Product 1

HCID 18506137HCID 18506137, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[2-chloro-6-(3-nitrobenzoylamino)phenoxy]benzenesulfonic acid 2,2-dimethyl-propyl ester (52 mg, 0.10 mmol) and tetraethyl ammonium chloride (54 mg, 0.5 mmol) in DMF (5 ml) was stirred at reflux temperature for 24 hours. The reaction mixture was evaporated and purified on preparative HPLC (Gilson semi-prep.column prep-NOVA-PaK®HRC18, 6 microM, 60 Å; Flow 15 ml/min Gradient: 5-100% MeCN in water (20 min)) to give 4-[2-chloro-6-(3-nitrobenzoylamino)phenoxy]benzenesulfonic acid (yield 22 mg (25%)). LC/MS: m/e 449 (M+).

Workup

  1. temperatureat reflux temperature for 24 hours
  2. customThe reaction mixture was evaporated
  3. custompurified on preparative HPLC (Gilson semi-prep.column prep-NOVA-PaK®HRC18, 6 microM, 60 Å; Flow 15 ml/min Gradient: 5-100% MeCN in water (20 min))

Sources & evidence

ORD record
ord-85552d5bc9a24b718e12f3c9f3e8a9b3
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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