Sodium Azide → HCID 86610766, compound

HRID 2240073Notes

Reaction equation

HRID 2240073 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([O:18][CH2:19][CH2:20]Cl)[C:12]=2[NH2:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CS(C)=O.O>[N:23]([CH2:20][CH2:19][O:18][C:13]1[CH:14]=[C:15]([F:17])[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[NH2:22])=[N+:24]=[N-:25]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 68677992HCID 68677992, compound

Product 1

HCID 86610766HCID 86610766, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-benzenesulfonylmethyl-6-(2-chloro-ethoxy)-4-fluorophenylamine (1.67 g, 4.87 mmoles) and sodium azide (0.38 g, 5.84 mmoles) in DMSO (20 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 to afford the title compound as an off white solid (1.44 g, 4.14 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

Sources & evidence

ORD record
ord-cf2e4e3955c04b01a2130e020e40723c
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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