Sodium Azide → HCID 178514598, compound

HRID 2240051Notes

Reaction equation

HRID 2240051 reaction equation
ClC1C=C(C=CC=1)C[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:16][CH2:17]Cl)[C:8]([S:19]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[N:7]1.[N-:35]=[N+:36]=[N-:37].[Na+]>CS(C)=O.O>[N:35]([CH2:17][CH2:16][O:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[NH:6][N:7]=[C:8]2[S:19]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:21])=[N+:36]=[N-:37]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59304172HCID 59304172, compound

Product 1

HCID 178514598HCID 178514598, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(3-chloro-benzyl)-7-(2-chloro-ethoxy)-3-(naphthalene-1-sulfonyl)-1-H-indazole (0.25 g, 0.49 mmoles) and sodium azide (0.04 g, 0.58 mmoles) in DMSO (3 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 (0.23 g, 0.44 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-519cd0a7b4cd402393797d784da4d887
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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