1,3-Diisocyanatobenzene → HCID 10101783, compound

HRID 2415117Notes

Reaction equation

HRID 2415117 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][CH2:21][CH2:22][CH3:23].[C:24]1([N:33]=[C:34]=[O:35])[CH:29]=[CH:28][CH:27]=[C:26]([N:30]=[C:31]=[O:32])[CH:25]=1>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[C:24]1([NH:33][C:34]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]=[C:10]([NH2:19])[C:9]=3[N:8]=[C:7]2[CH2:20][CH2:21][CH2:22][CH3:23])=[O:35])[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]=[C:10]([NH2:19])[C:9]=3[N:8]=[C:7]2[CH2:20][CH2:21][CH2:22][CH3:23])=[O:32])[CH:25]=1

Participants

5

Reactant 2

HCID 312621,3-DiisocyanatobenzeneHCID 155382261-(4-Aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10101783HCID 10101783, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A suspension of 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (3.11 g, 10.0 mmol) in 100 mL of CH2Cl2 was treated with 1,3-phenylene diisocyanate (800 mg, 5.0 mmol) and stirred under N2 overnight. The reaction mixture was then concentrated under reduced pressure to give a white solid. The white solid was then dissolved in 150 mL of hot 15% MeOH/CHCl3. After slow evaporation of the solvent, a white precipitate had formed. The solid was isolated by filtration, washed with 10% MeOH/CHCl3 (3×10 mL) and dried under vacuum to give the desired product (400 mg) as a white powder. M. p. 160.3-165.6° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.34 (s, 2H), 8.01 (d, J=7.9 Hz, 2H), 7.60 (d, J=8.3 Hz, 2H), 7.43 (s, 1H), 7.38 (t, J=7.6 Hz, 2H), 7.22 (t, J=7.0 Hz, 2H), 7.05-6.94 (m, 3H), 6.45 (s, 4H), 6.07 (t, J=5.4 Hz, 2H) 4.53 (t, J=7.4 Hz, 4H), 3.15 (m, 4H), 2.92 (t, J=7.7 Hz, 4H), 1.88-1.74 (m, 8H), 1.66 (m, 4H), 1.43 (m, 4H), 0.92 (t, J=7.3 Hz, 6H);

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give a white solid
  3. customAfter slow evaporation of the solvent
  4. customa white precipitate had formed
  5. customThe solid was isolated by filtration
  6. washwashed with 10% MeOH/CHCl3 (3×10 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4fb476218ea64d30951dd5e56a625a48
Source dataset
uspto-grants-2004_11
Patent number
US06818650B2

Reaction notes

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