Dansyl chloride → HCID 23445292, compound

HRID 1166923Notes

Reaction equation

HRID 1166923 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:18][C:19]1[C:20]([CH3:36])=[N:21][O:22][C:23]=1[NH:24][S:25]([C:28]1[CH:32]=[CH:31][S:30][C:29]=1[C:33]([NH2:35])=[O:34])(=[O:27])=[O:26].[H-].[Na+]>O>[Br:18][C:19]1[C:20]([CH3:36])=[N:21][O:22][C:23]=1[NH:24][S:25]([C:28]1[CH:32]=[CH:31][S:30][C:29]=1[C:33]([NH:35][S:1]([C:4]1[C:16]2[C:8](=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2])=[O:34])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 10546830HCID 10546830, compound

Product 1

HCID 23445292HCID 23445292, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dansylchloride (90.2 mg, 0.328 mmol) was added to a solution of N-(4-bromo-3-methyl-5-isoxazolyl)-2-(aminocarbonyl)thiophene-3-sulfonamide (Example 89) (100 mg, 0.273 mmol) and NaH (43.7 mg, 60% dispersion in mineral oil, 1.10 mmol). The reaction was stirred at room temperature for 1 hour. Water was added to quench the reaction and THF was stripped off on a rotavap. The aqueous residue was partitioned between 1 N HCl and EtOAc. The organic layer was dried (MgSO4). The solid was filtered and the filtrate concentrated. The residue was recrystallized from EtOAc to give N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(5-dimethylamino-1-naphthyl)sulfonylaminocarbonyl]thiophene-3-sulfonamide (55 mg., 34% yield) as a white powder (m.p. 184-186° C.).

Workup

  1. customto quench
  2. customthe reaction and THF
  3. customwas stripped off on a rotavap
  4. customThe aqueous residue was partitioned between 1 N HCl and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationThe solid was filtered
  7. concentrationthe filtrate concentrated
  8. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-2a76c82f338e401b937cb8c555db7097
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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