Sodium Azide → HCID 18969573, compound

HRID 399015Notes

Reaction equation

HRID 399015 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]2[C:6]=1[CH2:7][C:8](=[O:15])[NH:9]2.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]2[C:6]=1[CH2:7][C:8](=[O:15])[NH:9]2)=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10704607HCID 10704607, compound

Product 1

HCID 18969573HCID 18969573, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-chloroethoxy)-7-fluoro-1,3-dihydro-indol-2-one (2.04 g, 8.88 mmol) and sodium azide in dimethylformamide (125 mL) was heated to 70° C. for 18 hours. The reaction mixture was partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer separated and washed with water (50 mL) then dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum. The crude product was filtered through a pad of silica to afford a yellow solid, mp 147°-148° C. MS EI m/e 261 (M+).

Workup

  1. customThe reaction mixture was partitioned between methylene chloride (100 mL) and water (100 mL)
  2. customThe organic layer separated
  3. washwashed with water (50 mL)
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. filtrationThe crude product was filtered through a pad of silica
  8. customto afford a yellow solid, mp 147°-148° C

Sources & evidence

ORD record
ord-98bf740990c644b294960542a130f29d
Source dataset
uspto-grants-1998_10
Patent number
US05817690

Reaction notes

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