Chloride → HCID 18448589, compound

HRID 32051Notes

Reaction equation

HRID 32051 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].C1(C)C=CC=CC=1.[Cl-]>CN(C=O)C>[N:14]([CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1)=[N+:15]=[N-:16]

Participants

6

Reactant 4

HCID 312ChlorideHCID 1140TolueneHCID 33557Sodium AzideHCID 18448592HCID 18448592, compound

Product 1

HCID 18448589HCID 18448589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-7-cyanochroman (Step C) (8.1 g, 42 mmol) was dissolved in dry DMF (90 mL) and NaN3 (4.0 g, 62 mmol) was added and the reaction was heated to 80° C. under N2. After 5 h TLC (SiO2, toluene) showed that no starting chloride was present. The reaction was cooled and partitioned between EtOAc (200 mL) and H2O (150 mL). The organic phase was washed with H2O (2×100 mL) and brine (100 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 15% EtOAc in hexane) to provide the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc (200 mL) and H2O (150 mL)
  3. washThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (SiO2, 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-98fd8387528a469cbcf5e2db00cdee14
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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