Dimethylamine → HCID 10567786, compound

HRID 378307Notes

Reaction equation

HRID 378307 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14](Br)[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:21][NH:22][CH3:23]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([N:22]([CH3:23])[CH3:21])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 674Dimethylamine2×HCID 10689660HCID 10689660, compound

Product 1

HCID 10567786HCID 10567786, compoundYield 8%

Procedure

2.5 g (0.007 mol) of 4-amino-N-(2-bromo-6-methylamino-pyridin-4-yl)-benzenesulfonamide were stirred with 80 ml of dimethylamine in an autoclave at 160° C. for 7 hours. The residual dimethylamine was left to evaporate and the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1, then 2:1 and finally 3:1. The polar fractions were chromatographed twice on silica gel with ethyl acetate/hexane 2:3 and 1:1 as the eluent. There was obtained 0.175 g (8%) of 4-amino-N-(2-dimethylamino-6-methylamino-pyridin-4-yl)-benzenesulfonamide as beige crystals: MS (ISP): me/e=322 (C14H20N5O2S+).

Workup

  1. customto evaporate
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:1
  3. customThe polar fractions were chromatographed twice on silica gel with ethyl acetate/hexane 2:3 and 1:1 as the eluent

Sources & evidence

ORD record
ord-2ec3785666fb45189c8785e5ed3103f6
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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