Sodium Cyanide → 2-Cyanomethyl-3-octadecylcarbamoyloxypropyl benzoate

HRID 728501Notes

Reaction equation

HRID 728501 reaction equation
[C:1]([O:9][CH2:10][CH:11]([CH2:35]Br)[CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].C(OCC(C[C:70]#[N:71])COCCCCCCCCCCCCCCCC)(=O)C1C=CC=CC=1>CS(C)=O>[C:1]([O:9][CH2:10][CH:11]([CH2:35][C:70]#[N:71])[CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 538844692-Bromomethyl-3-n-octadecylcarbamoyloxypropyl benzoateHCID 545411872-Cyanomethyl-3-hexadecyloxypropyl benzoate

Product 1

HCID 541175562-Cyanomethyl-3-octadecylcarbamoyloxypropyl benzoateYield 95.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.76 g (3.10 mM) of 2-bromomethyl-3-n-octadecylcarbamoyloxypropyl benzoate, 185 mg (3.26 mM) of 95% sodium cyanide in 30 ml of dimethylsulfoxide is allowed to react by the same procedure as described in the (136) and 1.49 g (95.5% yield) of the titled compound n5' is obtained.

Workup

  1. customto react by the same procedure

Sources & evidence

ORD record
ord-c2a24b7fd029413e8c77dc182d89261c
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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