Lithium azide → 1-Azido-2-cyanomethyl-3-hexadecyloxypropane

HRID 728497Notes

Reaction equation

HRID 728497 reaction equation
[N-:1]=[N+:2]=[N-:3].[Li+].CS(O[CH2:10][CH:11]([CH2:30][C:31]#[N:32])[CH2:12][O:13][CH2:14][CH2:15][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][CH3:29])(=O)=O.N(CC(NC(OC)=O)CSCCCCCCCCCCCCCCCC)=[N+]=[N-]>CN(C)C=O>[N:1]([CH2:10][CH:11]([CH2:30][C:31]#[N:32])[CH2:12][O:13][CH2:14][CH2:15][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][CH3:29])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 88163Lithium azideHCID 148350943-Azido-1-hexadecylthio-2-methoxycarbonylaminopropaneHCID 230565432-Cyanomethyl-3-hexadecyloxypropyl methanesulfonate

Product 1

HCID 198842081-Azido-2-cyanomethyl-3-hexadecyloxypropaneYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 4.9 g (100 mM) of lithium azide, crude product of 2-cyanomethyl-3-hexadecyloxypropyl methanesulfonate Vn1a obtained in the previous reaction in 30 ml of dimethylformamide is converted by the same procedure as described in the (52) and 3.504 g (96.1% yield) of the titled compound Vn1a is obtained.

Sources & evidence

ORD record
ord-7cb9f55e51c74e0c95a6d77d24ad97fe
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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