Sodium Azide → HCID 86609129, compound

HRID 902341Notes

Reaction equation

HRID 902341 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[C:23]([C:24]4[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:31])[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:32]=[N+:33]=[N-:34].[Na+]>CS(C)=O>[N:32]([CH2:12][C@@H:13]1[O:14][C:15]2[C:23]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[CH:22][CH:21]=[CH:20][C:16]=2[CH2:17][CH2:18][CH2:19]1)=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609127HCID 86609127, compound

Product 1

HCID 86609129HCID 86609129, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of [(2R)-9-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1-benzoxepin-2-yl]methyl 4-methylbenzenesulfonate (381 mg, 0.798 mmol) and sodium azide (208 mg, 3.192 mmol) in anhydrous dimethyl sulfoxide (10 mL) was heated at 70° C. under nitrogen for 19 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 5 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 a colorless syrup. Purification by flash chromatography using 3% ethyl acetate in hexane as eluant gave 240 mg (86%) of (2R)-2-azidomethyl-9-(2,6-dichloro-phenyl)-2,3,4,5-tetrahydro-benzo[b]oxepine as 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
  9. customto afford a colorless syrup
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-346cd8709d184d76964f8a9e92fbede8
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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