Tert-Butylamine → HCID 22180784, compound

HRID 1796074Notes

Reaction equation

HRID 1796074 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]([NH2:13])([CH3:12])([CH3:11])[CH3:10]>CS(C)=O.O>[Br:8][C:4]1[N:3]=[C:2]([NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 122742,6-Dibromopyridine

Product 1

HCID 22180784HCID 22180784, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2,6-dibromopyridine (4.0 g, 16.5 mmol) and tert-butylamine (1.8 ml, 17.2 mmol) in dimethylsulfoxide (10 ml) was heated at 100° C. in a sealed tube for 20 h. After cooling to ambient temperature the reaction was diluted with water and extracted into dichloromethane. Combined organic extracts were washed with water and saturated brine then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel eluting with 20% diethyl ether in isohexane gave 6-bromo-N-(tert-butyl)pyridin-2-ylamine (0.4 g) as a solid: δH (360 MHz, CDCl3) 1.40 (9H, s), 6.34 (1H, d, J 8), 6.66 (1H, d, J 8), 7.18 (1H, dd, J 8 and 8); m/z (ES+) 229/231 (M++H).

Workup

  1. extractionextracted into dichloromethane
  2. washCombined organic extracts were washed with water and saturated brine
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a solid
  7. customPurification by chromatography on silica gel eluting with 20% diethyl ether in isohexane

Sources & evidence

ORD record
ord-22004b8b09e448a2854794c6b23a8804
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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