Dimethylformamide → HCID 11789689, compound

HRID 2186497Notes

Reaction equation

HRID 2186497 reaction equation
Cl[CH2:2][C@H:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N-:11]=[N+:12]=[N-:13].[Na+].CN(C=O)C>C1(C)C=CC=CC=1>[N:11]([CH2:2][C@H:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 27344454-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

Product 1

HCID 11789689HCID 11789689, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a 200 ml four-necked flask were charged 20.0 g (0.12 mol) of ethyl (R)-4-chloro-3-hydroxybutyrate, 15.6 g (0.24 mol) of sodium azide and 80 ml of DMF, and the reaction mixture was stirred for 24 hours at a reaction temperature of about 100° C. After cooling the reaction mixture, the reaction mixture was diluted with 100 ml of toluene, washed with 50 ml of water, and concentrated to give 16.5 g (79%) of the title compound.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwashed with 50 ml of water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7bef6720545a43558abd45b39df2490e
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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