Sodium Azide → HCID 10943006, compound

HRID 2179944Notes

Reaction equation

HRID 2179944 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[N-:12]=[N+:13]=[N-:14].[Na+]>CS(C)=O.O>[N:12]([CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5])=[N+:13]=[N-:14]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 642409(1R)-3-chloro-1-phenylpropan-1-ol

Product 1

HCID 10943006HCID 10943006, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

(R)-α-(2-Chloroethyl)benzenemethanol (0.73 g, 4.3 mmol) and sodium azide (417 mg, 1.5 eq.) in DMSO (3 ml) was stirred and heated at 40° C. for 1.5 h. The reaction mixture was diluted with water (50 ml) and the products extracted into ethyl acetate(2×75 ml). The combined extracts were dried (magnesium sulphate) and concentrated to an oil. Purification was achieved on silica gel eluting with 50% diethyl ether/isohexane to afford the azide as a colourless oil (0.6 g, 79%).

Workup

  1. extractionthe products extracted into ethyl acetate(2×75 ml)
  2. dry with materialThe combined extracts were dried (magnesium sulphate)
  3. concentrationconcentrated to an oil
  4. customPurification

Sources & evidence

ORD record
ord-5d8b0b1370a243259c45c74285d3d919
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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