Hydrochloric Acid → 5-dimethylamino-N-(5-bromo-6-chloro-2-pyrazinyl)-1-naphthalenesulphonamide

HRID 343372Notes

Reaction equation

HRID 343372 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([Br:8])=[C:4]([Cl:9])[N:3]=1.[H-].[Na+].[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].Cl>C(COC)OC.O>[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:1][C:2]1[CH:7]=[N:6][C:5]([Br:8])=[C:4]([Cl:9])[N:3]=1)(=[O:28])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 181802075-Bromo-6-chloropyrazin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 187047805-dimethylamino-N-(5-bromo-6-chloro-2-pyrazinyl)-1-naphthalenesulphonamideYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Amino-5-bromo-6-chloropyrazine (0.417 g) was added to a stirred suspension of sodium hydride (oil-free; 0.24 g) in dry dimethoxyethane (20 ml). When evolution of hydrogen ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.594 g) was added. The mixture was stirred for 24 hours and then water (25 ml) and 2M hydrochloric acid (2 ml) were added. The mixture was extracted with ethyl acetate (2×25 ml) and the extracts were dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column to give 5-dimethylamino-N-(5-bromo-6-chloro-2-pyrazinyl)-1-naphthalenesulphonamide (0.46 g), m.p. 180°-182° C. (after trituration with ether); mass spectrum (+ve FAB, methanol/NBA): 442 (M+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×25 ml)
  2. dry with materialthe extracts were dried (MgSO4)
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-f17097e3066a42538a61eb286182a9b2
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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