Phenyl isocyanate → HCID 11741838, compound

HRID 1837566Notes

Reaction equation

HRID 1837566 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:26])[C:16]=2[N:15]=[C:14]1[CH2:27][CH3:28].[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[NH2:26][C:17]1[C:16]2[N:15]=[C:14]([CH2:27][CH3:28])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:36]([NH:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:37])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 22344443HCID 22344443, compound

Product 1

HCID 11741838HCID 11741838, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.59.mL, 4.3 mmol) was added to a solution of 1-(4-aminobutyl)-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (1.00 g, 3.5 mmol) in chloroform (100 mL). The solution was stirred in an ice bath for 5 min. Phenyl isocyanate (0.38 mL, 3.5 mmol) was slowly added. The resulting precipitate was isolated by filtration, washed with chloroform (4×30 mL), and then dried in an Abderhalden drying apparatus overnight to provide 1.11 g of N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-phenylurea as a white solid, m.p. 179.7-181.4° C. Analysis: Calculated for C23H26N6O.. 0.6 H2O: %C, 66.84; %H, 6.63; %N, 20.33; Found: %C, 67.20; %H, 6.61; %N, 20.46.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with chloroform (4×30 mL)
  3. customdried in an Abderhalden drying apparatus overnight

Sources & evidence

ORD record
ord-e7050d43ee3c49409e275c9f019e7e1a
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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