11,12-Bis(8-isocyanatooctyl)docosane → HCID 178442887, compound

HRID 1158550Notes

Reaction equation

HRID 1158550 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][C:6](=[O:8])[N:7]=1.[N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([CH:40]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][N:59]=[C:60]=[O:61])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:19]=[O:20]>N1C=CC=CC=1>[CH2:30]([CH:29]([CH:40]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:60]([NH:1][C:2]1[NH:3][C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][C:6](=[O:8])[N:7]=1)=[O:61])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:18][C:19]([NH:1][C:2]1[NH:3][C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][C:6](=[O:8])[N:7]=1)=[O:20])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 5951299811,12-Bis(8-isocyanatooctyl)docosaneHCID 178442731HCID 178442731, compound

Product 1

HCID 178442887HCID 178442887, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

In a 250 mL round-bottomed flask was added 2-amino-6-nonylpyrimidin-4(1H)-one (1.88 g, 7.92 mmol) in Pyridine 50 mL to give a white suspension. The mixture was heated to 50 deg/C. 11,12-bis(8-isocyanatooctyl)docosane (2.327 g, 3.77 mmol) was dissolved in 5-10 mL of pyridine and added all at once to the mixture. The reaction was heated to 75 deg/C. and stirred for 24 h. The pyridine was removed and the residue was taken up in chloroform and the viscous solution was dripped into a rapidly stirring solution (500 mL) of MeOH upon which a white solid formed. The solution was decanted off and the residue was taken up in MeOH (10 ml) and rapidly stirred for 1 h. The product was collected by vacuum filtration dried under vacuum to give 4 g of 1,1′-(9,10-didecyloctadecane-1,18-diyl)bis(3-(6-nonyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea).

Workup

  1. customto give a white suspension
  2. temperatureThe mixture was heated to 50 deg/C
  3. additionadded all at once to the mixture
  4. temperatureThe reaction was heated to 75 deg/C
  5. customThe pyridine was removed
  6. customformed
  7. customThe solution was decanted off
  8. stirringrapidly stirred for 1 h
  9. filtrationThe product was collected by vacuum filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-19d58ade60d14e67b17ad9b14f067723
Source dataset
uspto-grants-2010_10
Patent number
US07811370B2

Reaction notes

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