Sodium Azide → 2-Azidomethyl-8-(2-chloro-phenyl)-chroman

HRID 902292Notes

Reaction equation

HRID 902292 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O.C(OCC)C>[N:30]([CH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[CH:17]=[CH:18][CH:19]=2)[O:14]1)=[N+:31]=[N-:32]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86609095[8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 866090972-Azidomethyl-8-(2-chloro-phenyl)-chromanYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A solution of [8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate, prepared in Example 1, step 7 (0.25 g, 0.58 mmol) and sodium azide (0.15 g, 2.3 mmol) in anhydrous dimethyl sulfoxide (9.5 mL) was heated to 70° C. under nitrogen for 16 hours. The cooled reaction mixture was then diluted with diethyl ether (50 mL), washed with water (5×25 mL) and saturated brine (25 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 0.14 g (82%) of 2-azidomethyl-8-(2-chloro-phenyl)-chroman as a colorless oil that was used without further purification.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (5×25 mL) and saturated brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-408ed90f443240d298654565d74be987
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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