Sodium Azide → HCID 59773586, compound

HRID 2220751Notes

Reaction equation

HRID 2220751 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([CH2:16][CH2:17]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[N:29]([CH2:17][CH2:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:8][C:9]=2[CH:15]=1)=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59773380HCID 59773380, compound

Product 1

HCID 59773586HCID 59773586, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Tosylate 191 (0.2 g) was dissolved in DMF (10 mL) and NaN3 (99 mg) was added as a solid. A condenser was affixed under nitrogen, and the mixture was heated to 50° C. for 16 h. The reaction was cooled to rt before being extracted with EtOAc. The organic layer was rinsed several times with water to ensure complete removal of DMF. The organic layer was then separated and dried over Na2SO4 before the solvent was removed under reduced pressure to give 192.

Workup

  1. customA condenser was affixed under nitrogen
  2. temperatureThe reaction was cooled to rt
  3. extractionbefore being extracted with EtOAc
  4. washThe organic layer was rinsed several times with water
  5. customremoval of DMF
  6. customThe organic layer was then separated
  7. dry with materialdried over Na2SO4 before the solvent
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-7da18d4669374925bb8374921e5a8640
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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