HCID 59512998, compound → HCID 178442888, compound

HRID 1158549Notes

Reaction equation

HRID 1158549 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]([CH3:53])=[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]([CH3:53])=[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]([CH3:53])=[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 59512998HCID 59512998, compoundHCID 178429414HCID 178429414, compound

Product 1

HCID 178442888HCID 178442888, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 250 mL round-bottomed flask fitted with a reflux condenser was added 11,12-bis(8-isocyanatooctyl)docosane (diamer diisocyanate, Cognis Corp.) (11.74 g, 19.03 mmol) and 2-amino-6-methylpyrimidin-4(1H)-one (5 g, 40.0 mmol) in Pyridine (50 mL) to give a white suspension. The mixture was heated to 95 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 about 100 ml and the viscous solution was poured into a rapidly stirring solution (1.5 L) of MeOH upon which a white solid formed. The white powder was collected by vacuum filtration and dried at 50 deg for 24 h to give 1,1′-(9,10-didecyloctadecane-1,18-diyl)bis(3-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea) (14.8 g)

Workup

  1. customIn a 250 mL round-bottomed flask fitted with a reflux condenser
  2. customto give a white suspension
  3. temperatureThe mixture was heated to 95 deg/C
  4. customThe pyridine was removed
  5. filtrationThe hazy solution was filtered
  6. concentrationthe resulting clear solution was concentrated to about 100 ml
  7. additionthe viscous solution was poured into a rapidly stirring solution (1.5 L) of MeOH upon which a white solid
  8. customformed
  9. filtrationThe white powder was collected by vacuum filtration
  10. customdried at 50 deg for 24 h

Sources & evidence

ORD record
ord-b26fc8408d454d44a4b944eb5986fcac
Source dataset
uspto-grants-2010_10
Patent number
US07811370B2

Reaction notes

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