Lithium azide → HCID 11779269, compound

HRID 1006595Notes

Reaction equation

HRID 1006595 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1.[N-:22]=[N+:23]=[N-:24].[Li+]>CN1CCCC1=O.O>[N:22]([CH2:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 88163Lithium azideHCID 10268183HCID 10268183, compound

Product 1

HCID 11779269HCID 11779269, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Chloromethyl-1(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (2.5 g; 0.0077 mol, Example 10) was suspended in N-methylpyrrolidone (15 mL). A solution of lithium azide (2.3 g) in water (45 mL) was added to the suspension. The resulting mixture was heated on the steam bath for 2 hr and then diluted with water (about 45 mL). The tan solid was washed with water and dried to yield 1.4 g (60.9%) of crude product. The solid was recrystallized from ethanol to give a pure product m.p. 174-178° C. Analysis: C, 61.0; H, 5.8; N, 33.2. Found: C, 60.9; H, 5.6; N, 32.6.

Workup

  1. temperatureThe resulting mixture was heated on the steam bath for 2 hr
  2. washThe tan solid was washed with water
  3. customdried
  4. customto yield 1.4 g (60.9%) of crude product
  5. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-701662e0fce843d4a3438e21dd13c8d6
Source dataset
uspto-grants-2004_09
Patent number
US06790961B2

Reaction notes

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