Methanol → 3-Phenylthio-2-hydroxypropylazide

HRID 2294349Notes

Reaction equation

HRID 2294349 reaction equation
[C:1]1([S:7][CH2:8][CH:9]2[CH2:11][O:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:12]=[N+:13]=[N-:14].[Na+].C(OC)=O.CO>O>[C:1]1([S:7][CH2:8][CH:9]([OH:10])[CH2:11][N:12]=[N+:13]=[N-:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7865Methyl formateHCID 33557Sodium AzideHCID 110949982-((Phenylsulfanyl)methyl)oxirane

Product 1

HCID 214747633-Phenylthio-2-hydroxypropylazideYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 7.2 g of phenylthiomethyloxirane (prepared as described in Preparation 85), 14 g of sodium azide, 65 ml of methyl formate and 270 ml of an 8:1 by volume mixture of methanol and water were used, to give 8.33 g of the title compound as a colorless oil having an Rf value of 0.23 (on silica gel thin layer chromatography, using a 1:10 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-12e8e3cc091e494b885bd119f6b80311
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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