Ethylamine → HCID 19353515, compound

HRID 378306Notes

Reaction equation

HRID 378306 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.[CH2:21]([NH2:23])[CH3:22]>>[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]([NH:23][CH2:21][CH3:22])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6341Ethylamine2×HCID 10689660HCID 10689660, compound

Product 1

HCID 19353515HCID 19353515, compoundYield 2.5%

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 ethylamine in an autoclave at 160° C. for 40 hours. The residual ethylamine was left to evaporate and the residue was chromatographed on silica gel with ethyl acetate/hexane 1:2, then 2:3 and finally 1:1. The thus-obtained 0.67 g of brown oil was suspended in 200 ml of 1N NaOH, suction filtered and the filtrate was neutralized with 1N HCl. It was again suction filtered, the filtrate was saturated with NaCl and extracted with ethyl acetate. The organic phase was dried. There was obtained 0.055 g (2.5%) of 4-amino-N-(2-ethylamino-6-methylamino-pyridin-4-yl)-benzenesulfonamide as pale brown crystals; MS (ISN): me/e=320 (C14H18N5O2S-).

Workup

  1. customto evaporate
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2
  3. filtrationsuction filtered
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was dried

Sources & evidence

ORD record
ord-1f22027a6cb4455ab072b1ff0bd78609
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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