Hydrogen Bromide → HCID 22253387, compound

HRID 1612380Notes

Reaction equation

HRID 1612380 reaction equation
[CH3:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:3]=1[O:4][C:5]1[C:10]([NH2:11])=[C:9]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:8]=[C:7]([CH3:18])[N:6]=1.Br.[N:26]([O-])=O.[Na+].[OH-].[NH4+]>O>[CH2:14]([CH:13]([N:12]1[C:9]2[CH:8]=[C:7]([CH3:18])[N:6]=[C:5]([O:4][C:3]3[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=3[CH3:1])[C:10]=2[N:11]=[N:26]1)[CH2:16][CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 219121512-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 22253387HCID 22253387, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamine (640 mg, 1.95 mmol) and 7 ml of 48% hydrobromic acid was added a solution of sodium nitrite (146 mg, 2.11 mmol) in 2 ml of water dropwise over 5 min at 0° C. The resulting mixture was treated with cuprous bromide Cu(I)Br (145 mg, 1.01 mmol) and then heated at reflux for 15 min. The mixture was cooled to room temperature and diluted with water, basified with ammonium hydroxide and extracted twice with ethyl acetate. The organic layer was dried and concentred to give 710 mg (93% yield) of the title compound as brown crystals, which was further recrystallized from isopropyl ether to give the title compound as golden crystals. 1H NMR (CDCl3) δ 6.92(s,2H), 6.84(s,1H), 4.5(m,1H), 2.40(s,3H), 2.32(s,3H), 2.13(s,6H), 2.0–2.4(m,4HO, 0.83(t,6H)ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 min
  3. extractionextracted twice with ethyl acetate
  4. customThe organic layer was dried

Sources & evidence

ORD record
ord-7164ee5b4b354c36a9b5ca7c97a1e902
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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