Methanol → 3-(N-Methyl-N-phenylamino)-2-hydroxypropylazide

HRID 1901737Notes

Reaction equation

HRID 1901737 reaction equation
[CH3:1][N:2]([CH2:9][CH:10]1[CH2:12][O:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+].C(OC)=O.CO>O>[CH3:1][N:2]([CH2:9][CH:10]([OH:11])[CH2:12][N:13]=[N+:14]=[N-:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 96044N-methyl-N-(oxiran-2-ylmethyl)aniline

Product 1

HCID 214747453-(N-Methyl-N-phenylamino)-2-hydroxypropylazideYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 1.65 g of N-methyl-N-phenylaminomethyloxirane (prepared as described in Preparation 88), 3.29 g of sodium azide, 15 ml of methyl formate and 63 ml of an 8:1 by volume mixture of methanol and water were used, to give 1.9 g of the title compound as a pale yellow oil having an Rf value of 0.09 (on silica gel thin layer chromatography, using a 1:15 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 12

Sources & evidence

ORD record
ord-0b7c5a1f87c94c88ab3019ed19bc25d7
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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