Toluene → HCID 178482595, compound

HRID 554362Notes

Reaction equation

HRID 554362 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:32][N:24]([CH2:23][C:14]1[CH:15]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]([S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]3[NH:35][N:34]=[N:33][N:2]=3)[CH:4]=2)(=[O:10])=[O:11])[CH:13]=1)[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 66924754HCID 66924754, compound

Product 1

HCID 178482595HCID 178482595, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl ({1-[(3-cyanophenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (0.29 g), sodium azide (70 mg), triethylamine hydrochloride (0.19 g) and toluene (10 ml) was heated under reflux for 7 days. After cooling the reaction mixture, ethyl acetate was added to the mixture, and the mixture was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=10:1) to give the title compound as an oil (yield 0.052 g, 16%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 days
  3. additionwas added to the mixture
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-methanol=10:1)

Sources & evidence

ORD record
ord-d22f39fb31c84c5c91d3e7ccd59369bc
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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