Sodium Azide → N-(2-Azido-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide

HRID 1750502Notes

Reaction equation

HRID 1750502 reaction equation
[CH3:1][C:2]12[N:7]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:6]1[CH2:5][CH2:4][CH2:3]2.[N-:18]=[N+:19]=[N-:20].[Na+]>CC(O)C.O>[N:18]([C:2]1([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[N+:19]=[N-:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 1180245801-Methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane

Product 1

HCID 118024623N-(2-Azido-2-methylcyclopentyl)-4-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane (55 g, 219.12 mmol) in IPA (1000 ml) and water (1000 ml) was added sodium azide (57.0 g, 876.92 mmol). The reaction mixture was stirred at room temperature for 17 hours. The reaction was cooled to room temperature and water (1000 ml) was added. The aqueous layer was extracted with diethyl ether (3×500 ml). The combined organics were washed with brine (250 ml), dried over sodium sulfate, concentrated in vacuo to afford the title compound.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe aqueous layer was extracted with diethyl ether (3×500 ml)
  3. washThe combined organics were washed with brine (250 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a57b1b43720d4f4dbb4dc58d259a1c78
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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