Ammonium Chloride → HCID 178420135, compound

HRID 1820840Notes

Reaction equation

HRID 1820840 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([O:22][CH2:23][C:24]#[N:25])[CH:16]=[CH:15]4)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([O:22][CH2:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)[CH:16]=[CH:15]4)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68981461HCID 68981461, compound

Product 1

HCID 178420135HCID 178420135, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of {[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetonitrile (204 mg, 0.596 mmol), prepared in the previous step, sodium azide (119 mg, 1.82 mmol) and ammonium chloride (98 mg, 1.82 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 5 h. The reaction was partitioned between 10% methanol-methylene chloride and 1 N HCl. The organic layer was separated, extracted three times with water, dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound (87 mg, 37%) as a white solid, mp 226-228° C. Elemental Analysis for C21H15N5OS+0.23 H2O Calc'd: C, 64.74; H, 4.00; N, 17.98. Found: C, 63.46; H, 4.08; N, 16.95

Workup

  1. customThe reaction was partitioned between 10% methanol-methylene chloride and 1 N HCl
  2. customThe organic layer was separated
  3. extractionextracted three times with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0cb4f18ac4f743b4bb58968c756ee2f2
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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