Ammonium Chloride → HCID 178513646, compound

HRID 2241167Notes

Reaction equation

HRID 2241167 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[C:15]([NH:17]C2C=CC(C#N)=CC=2)=[O:16])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+:30].[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O.[Na]>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13]([C:28]3[CH:27]=[CH:26][C:14]([C:15]4[NH:30][N:33]=[N:32][N:31]=4)=[CH:13][CH:12]=3)=[C:14]([CH:26]=[CH:27][CH:28]=2)[C:15]([NH2:17])=[O:16])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67549447HCID 67549447, compound

Product 1

HCID 178513646HCID 178513646, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 5360545SodiumSolvent

Procedure

A microwave vial was charged with a solution of 3-(3-chloro-benzenesulfonylamino)-N-(4-cyano-phenyl)-benzamide (0.46 g, 1.12 mmol) in dimethylformamide (20.0 ml), ammonium chloride (1.11 g, 21 mmol, 18.5 equiv.) and sodium azide (1.31 g, 20 mmol, 18 equiv.) and irradiated in a microwave oven at 155° C. for 75 min. The mixture was diluted with saturated sodium hydrogenocarbonate and the phases were separated. The aqueous phase was washed with ethyl acetate and the organic phases were discarded. The aqueous phase was acidified with HCl (1N) and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and the solvent removed in vacuo. The crude compound was triturated in dichloromethane and the white solid was filtered and dried under high vacuum. The title compound, MS (ISP): m/e=453.3 (M−H) was obtained as a white solid, 0.40 g (80%).

Workup

  1. customirradiated in a microwave oven at 155° C. for 75 min
  2. customthe phases were separated
  3. washThe aqueous phase was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude compound was triturated in dichloromethane
  9. filtrationthe white solid was filtered
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-f4c20387b3eb40679f9633ff56e2cc44
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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