Ammonium Chloride → HCID 57457055, compound

HRID 1361025Notes

Reaction equation

HRID 1361025 reaction equation
[C:1]([CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)#[N:2].[N-:14]=[N+:15]=[N-:16].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:2]1[NH:14][N:15]=[N:16][C:1]=1[CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 201149864-[(Cyanomethyl)sulfanyl]benzoic acid

Product 1

HCID 57457055HCID 57457055, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-cyanomethylsulfanylbenzoic acid (27.2 g, 0.14 mol), sodium azide (11.8 g, 0.18 mol) and ammonium chloride (9.7 g, 0.18 mol) in DMF (1000 mL) was refluxed overnight under N2. The mixture was concentrated in vacuo. The residue was suspended in cold water and extracted with diethyl ether. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. Water was added and the precipitate was filtered off. The aqueous layer was concentrated in vacuo, water was added and the precipitate filtered off. The combined impure products were purified by column chromatography using DCM:MeOH=9:1 as eluent, affording the title compound (5.2 g, 16%).

Workup

  1. temperaturewas refluxed overnight under N2
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionextracted with diethyl ether
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. additionWater was added
  8. filtrationthe precipitate was filtered off
  9. concentrationThe aqueous layer was concentrated in vacuo, water
  10. additionwas added
  11. filtrationthe precipitate filtered off
  12. customThe combined impure products were purified by column chromatography

Sources & evidence

ORD record
ord-e04c3cbe05ce4ac98a80b4b8b61b3ed7
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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