11,12-Bis(8-isocyanatooctyl)docosane → HCID 178442842, compound

HRID 1158551Notes

Reaction equation

HRID 1158551 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH:23]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][N:42]=[C:43]=[O:44])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:2]=[O:3].[NH2:45][C:46]1[NH:47][C:48]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:49][C:50](=[O:52])[N:51]=1>N1C=CC=CC=1>[CH2:13]([CH:12]([CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43]([NH:45][C:46]1[NH:47][C:48]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:49][C:50](=[O:52])[N:51]=1)=[O:44])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH:1][C:2]([NH:45][C:46]1[NH:47][C:48]([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:49][C:50](=[O:52])[N:51]=1)=[O:3])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 5951299811,12-Bis(8-isocyanatooctyl)docosaneHCID 178442843HCID 178442843, compound

Product 1

HCID 178442842HCID 178442842, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 250 mL round-bottomed flask fitted with a reflux condensor was added 11,12-bis(8-isocyanatooctyl)docosane (diamer diisocyanate, Cognis Corp.) (5.18 g, 8.39 mmol) and 2-amino-6-pentadecylpyrimidin-4(1H)-one (5.67 g, 17.63 mmol) in Pyridine (50 mL) to give a white suspension. The mixture was heated to 75 deg/C under argon and stirred for 24 h. The pyridine was removed and the residue was taken up in chloroform. The hazy solution was filtered and the resulting clear solution was concentrated to 50 ml and the viscous solution was poured into a rapidly stirring solution (1 L) of MeOH upon which a white solid formed. The solid was collected by filtration and dried under vacuum for 24 h to give 10.5 g 1,1′-(9,10-didecyloctadecane-1,18-diyl)bis(3-(4-oxo-6-pentadecyl-1,4-dihydropyrimidin-2-yl)urea)

Workup

  1. customIn a 250 mL round-bottomed flask fitted with a reflux condensor
  2. customto give a white suspension
  3. temperatureThe mixture was heated to 75 deg/C under argon
  4. customThe pyridine was removed
  5. filtrationThe hazy solution was filtered
  6. concentrationthe resulting clear solution was concentrated to 50 ml
  7. additionthe viscous solution was poured into a rapidly stirring solution (1 L) of MeOH upon which a white solid
  8. customformed
  9. filtrationThe solid was collected by filtration
  10. customdried under vacuum for 24 h

Sources & evidence

ORD record
ord-f4e632804cd0432090d72051ea3488a8
Source dataset
uspto-grants-2010_10
Patent number
US07811370B2

Reaction notes

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