Sodium Azide → HCID 86609110, compound

HRID 902313Notes

Reaction equation

HRID 902313 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([F:30])[CH:11]=[C:12]2[C:17]=1[O:16][CH:15]([CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:14][CH2:13]2.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:18][CH:15]1[CH2:14][CH2:13][C:12]2[C:17](=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:9]=[C:10]([F:30])[CH:11]=2)[O:16]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609109Toluene-4-sulfonic acid 8-(2-chloro-phenyl)-6-fluoro-chroman-2-ylmethyl ester

Product 1

HCID 86609110HCID 86609110, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of toluene-4-sulfonic acid 8-(2-chloro-phenyl)-6-fluoro-chroman-2-ylmethyl ester (253 mg, 0.566 mmol) and sodium azide (147 mg, 2.264 mmol) in anhydrous dimethyl sulfoxide (8 mL) was heated to 70° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 10 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 170 mg (95%) of 2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman a colorless syrup.

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched by the addition of water (30 mL)
  3. customThe mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customthe organic phase separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57c76d60b92c48a7af4887ad66e9af76
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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