Sodium Azide → 2-Phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphosphorinane

HRID 6336

Reaction equation

HRID 6336 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[O:5]([P:12]1(=[O:20])[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18]I)[O:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.CN(C=O)C>[O:5]([P:12]1(=[O:20])[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][N:1]=[N+:2]=[N-:3])[O:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 197931292-Phenoxy-2-oxo-6-iodomethyl-1,2-oxaphosphorinane

Product 1

HCID 197931202-Phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphosphorinaneYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 19608675Benzene dimethylformamideSolvent

Procedure

A suspension containing two equivalents of sodium azide, one equivalent of the above-prepared iodonated oxaphosphorinane and a catalytic amount of about 0.1 equivalent of tetrabutylammonium bromide in benzene/DMF (1:1) was heated to 60-80 degrees C. for 16 hours to produce 2-phenoxy-2-oxo-6-(azidomethyl)-1,2-oxaphosphorinane in 96 percent yield as a white solid.

Sources & evidence

ORD record
ord-e5f02821feab4e68bc5f37db01f810ce
Source dataset
uspto-grants-1993_09
Patent number
US05248611

Linked notes

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