Ammonium Chloride → HCID 58009360, compound

HRID 1009493Notes

Reaction equation

HRID 1009493 reaction equation
[Cl:1][C:2]1[C:3]([CH3:32])=[C:4]([N:8]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:32])=[C:4]([N:8]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:23])=[O:24])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:33]=[N:34][NH:35][N:21]=3)[CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 58009375HCID 58009375, compound

Product 1

HCID 58009360HCID 58009360, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

300 mg of N2-(3-chloro-2-methylphenyl)-N-(3-cyanobenzyl)-N2-[(4-methylphenyl)sulfonyl]glycinamide was dissolved in 5.00 mL of DMF, and 125 mg of sodium azide and 103 mg of ammonium chloride were added thereto, followed by stirring at 100° C. for 6 hours. The reaction liquid was concentrated under reduced pressure, and to the obtained residue was added water, followed by extraction with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by preparative thin layer chromatography (chloroform:methanol=80:20). The obtained product was recrystallized from ethanol/diisopropyl ether to obtain 82.6 mg of N2-(3-chloro-2-methylphenyl)-N2-[(4-methylphenyl)sulfonyl]-N-[3-(2H-tetrazol-5-yl)benzyl]glycinamide.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionto the obtained residue was added water
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by preparative thin layer chromatography (chloroform:methanol=80:20)
  9. customThe obtained product was recrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-f20d690309684627a2266160e4bb2a93
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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