Hydrochloric Acid → HCID 178456130, compound

HRID 427741Notes

Reaction equation

HRID 427741 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([Cl:24])=[CH2:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].C([NH+](CC)CC)C.Cl>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]([Cl:24])=[CH2:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:27][N:26]=[N:25][N:18]=2)=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 18357774HCID 18357774, compound

Product 1

HCID 178456130HCID 178456130, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-[N-(5-Bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]-5-cyanopyridine (reference example 7) (0.40 g, 0.96 mmol), in sieve-dried N-methyl pyrrolidone (10 ml) was treated with sodium azide (189 mg, 12.9 mmol) followed by triethylammonium chloride (208 mg, 1.49 mmol) and the mixture heated at 120° C. (oil bath) for 8 hours. The red solution was taken into ice/water (12 ml), acidified to pH 1-2 with concentrated hydrochloric acid, extracted with ethyl acetate (×2) and the combined extracts washed with water (×2), dried (MgSO4) and evaporated to give a pale red gum (0.45 g). The gum was presorbed to silica (1.2 g) and purified by MPLC to give a colourless title compound as a gum which solidified (135 mg, 31%).

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. washthe combined extracts washed with water (×2)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3382ad09477d4512af8b43ce1f5a64ea
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

Loading…