Sodium Azide → HCID 86610765, compound

HRID 2240071Notes

Reaction equation

HRID 2240071 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19]Cl)[C:12]=2[NH2:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CS(C)=O.O>[N:22]([CH2:19][CH2:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:12]=1[NH2:21])=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 68678931HCID 68678931, compound

Product 1

HCID 86610765HCID 86610765, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-benzenesulfonylmethyl-6-(2-chloro-ethoxy)-phenylamine (0.5 g, 1.53 mmoles) and sodium azide (0.15 g, 2.29 mmoles) in DMSO (10 mL) was stirred together in a round bottom flask under nitrogen at 90° C. for 3 hours. Reaction mixture was cooled to room temperature, diluted with water, extracted with EtOAC, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. Crude compound was purified by normal phase HPLC using as eluent 40% EtOAc/hexane to afford the title compound as an off white solid (0.39 g, 1.17 mmoles).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with EtOAC
  4. washwashed with water (2×), brine (1×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customCrude compound was purified by normal phase HPLC

Sources & evidence

ORD record
ord-5c4de244180f41a2bbc87a484238a728
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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