Dansyl chloride → HCID 23445292, compound

HRID 234410Notes

Reaction equation

HRID 234410 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 1N HCl and EtOAc. The organic layer was dried (MgSO4). The solid was filtered and the filtrate concentrated. The residue was recrystalized 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 1N 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 recrystalized from EtOAc

Sources & evidence

ORD record
ord-4968dfae992544c28e250218362a372f
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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