Ethyl isocyanate → HCID 86612254, compound

HRID 1623123Notes

Reaction equation

HRID 1623123 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[CH3:6][O:7][NH:8][CH:9]([CH3:29])[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]=[CH:17][C:16]=2[N:15]=[C:14]1[CH2:26][CH2:27][CH3:28]>O1CCCC1>[CH2:26]([C:14]1[N:13]([CH2:12][CH2:11][CH2:10][CH:9]([N:8]([O:7][CH3:6])[C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH3:29])[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=1)[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 86612250HCID 86612250, compound

Product 1

HCID 86612254HCID 86612254, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl isocyanate (0.49 mL, 4.59 mmol) was added to a solution of O-methyl-N-[1-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine (0.600 g, 1.83 mmol) in tetrahydrofuran (THF) (25 mL) at 0° C. and stirred for 1 hour at ambient temperature. Analysis by LC-MS showed the reaction was incomplete and additional ethyl isocyanate (0.19 mL) was added to the reaction mixture. After 1 hour of stirring at ambient temperature, the reaction mixture was concentrated under reduced pressure to afford 0.700 g of 1-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-3-ethyl-1-methoxyurea.

Workup

  1. stirringAfter 1 hour of stirring at ambient temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82468cb4ce5d4d4092fd1edcdac6a8c4
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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