Dansyl chloride → HCID 19040006, compound

HRID 1684561Notes

Reaction equation

HRID 1684561 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][N:5]=1.[H][H].[CH3:14][N:15]([CH3:30])[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[S:26](Cl)(=[O:28])=[O:27]>COCCOC>[CH3:14][N:15]([CH3:30])[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[S:26]([NH:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][N:5]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 778863,5-Dichloro-3-pyridylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 19040006HCID 19040006, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

Oil-free sodium hydride (48 mg) was added to a solution of 2-amino-3,5-dichloropyridine (326 mg) in 1,2-dimethoxyethane (20 ml). After evolution of hydrogen ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (540 mg) was added and the mixture was heated at 75° C. for 3 days. Volatile material was removed by evaporation and the residue was purified by flash chromatography. Elution with dichloromethane/hexane (3:2 v/v) and trituration of the resulting foam with ether/hexane (1:10 v/v) gave 5-(dimethylamino)-N-(3,5-dichloro-2-pyridyl)-1-naphthalenesulphonamide (52 mg), m.p. 161°-163° C.; mass spectrum [+ve FAB, dimethylsulphoxide (DMSO)/glycerol (GLY)]: 396 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was purified by flash chromatography
  3. washElution with dichloromethane/hexane (3:2 v/v) and trituration of the resulting foam with ether/hexane (1:10 v/v)

Sources & evidence

ORD record
ord-5280e79311df4bd28f36380f32203e68
Source dataset
uspto-grants-1997_06
Patent number
US05641793

Reaction notes

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