2,4-Difluorophenyl isocyanate → 1,4-Bis[[1-heptyl-3-(2,4-difluorophenyl)ureido]methyl]benzene

HRID 483928Notes

Reaction equation

HRID 483928 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N:33]=[C:34]=[O:35]>CCCCCC>[CH2:18]([N:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:34]([NH:33][C:27]2[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=2[F:25])=[O:35])=[CH:15][CH:14]=1)[C:34]([NH:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[F:25])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 14801556N,N'-diheptyl-p-xylylenediamine

Product 1

HCID 148015621,4-Bis[[1-heptyl-3-(2,4-difluorophenyl)ureido]methyl]benzeneYield 79.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a solution of 1.5 g N,N'-diheptyl-p-xylylenediamine in 20 ml n-hexane, was added dropwise with stirring 5 ml of a n-hexane solution containing 1.4 g 2,4-difluorophenyl isocyanate under ice cooling. Stirring was continued at room temperature for two hours, and the solid which separated out was collected by filtration and recrystallized from methanol, giving 2.3 g of 1,4-bis[[1-heptyl-3-(2,4-difluorophenyl)ureido]methyl]benzene.

Workup

  1. customthe solid which separated out
  2. filtrationwas collected by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6b72f57b074145729e0826d1b006e95e
Source dataset
uspto-grants-1993_07
Patent number
US05227492

Reaction notes

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