Dansyl chloride → HCID 11793037, compound

HRID 343359Notes

Reaction equation

HRID 343359 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].[NH2:18][C:19]1[N:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:18][C:19]1[N:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 11801Dansyl chlorideHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 11793037HCID 11793037, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 5-dimethylamino-1-naphthalenesulphonyl chloride (3.98 g), 3-amino-6-chloropyridazine (1.91 g) and 4-dimethylaminopyridine (100 mg) in pyridine (25 ml) was heated at 85° C for 18 hours. Volatile material was removed by evaporation and dichloromethane (50 ml) was added. Insoluble material was removed by filtration and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), and the resulting foam was crystallised from ether to give 5-(dimethylamino)-N-(6-chloro-3-pyridazinyl)-1-naphthalenesulphonamide (1.74 g), m.p. 153°-154° C.; mass spectrum (positive chemical ionisation ((+)ve CI)): 363 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation and dichloromethane (50 ml)
  2. additionwas added
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:1 v/v)
  7. customthe resulting foam was crystallised from ether

Sources & evidence

ORD record
ord-7685b28ca7ef4735bec45b83e4e62735
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

Loading…