1-Isocyanatotridecane → HCID 23039655, compound

HRID 2166439Notes

Reaction equation

HRID 2166439 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11](=[CH2:14])[CH2:12][OH:13])=[O:8].[CH2:15]([N:28]=[C:29]=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:15]([NH:28][C:29]([O:13][CH2:12][C:11](=[CH2:14])[CH2:10][O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 144646761-IsocyanatotridecaneHCID 23039626HCID 23039626, compound

Product 1

HCID 23039655HCID 23039655, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

3-(6-Bromohexanoyloxy)-2-methylenepropan-1-ol (from Preparation 44) (0.58 g), tridecyl isocyanate (0.55 g) and 4-dimethylaminopyridine (0.05 g) were mixed in methylene chloride (3 ml). After stirring for 23 hours at 22° C. the mixture was filtered, and the filtrate was purified through a column of silica gel 60 (70-230 mesh, 4 g) eluting with ether/chloroform 1:1. Further purification was achieved by chromatography on Waters PrepLC®/System 500A using a prepPAK®-500/SILICA cartridge with ether/chloroform/pentane 1:1:4 as eluent.

Workup

  1. filtrationwas filtered
  2. customthe filtrate was purified through a column of silica gel 60 (70-230 mesh, 4 g)
  3. washeluting with ether/chloroform 1:1
  4. customFurther purification

Sources & evidence

ORD record
ord-70987eae8f794e28ab24a6d724817247
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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