Hydrochloric Acid → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-aminophenyl)benzamide

HRID 323142Notes

Reaction equation

HRID 323142 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:35]=[CH:34][C:20]([C:21]([N:23]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4C(O)=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C1(P([N:50]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.Cl>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:35]=[CH:34][C:20]([C:21]([N:23]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[NH2:50])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 220109694-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxyphenyl)benzamide

Product 1

HCID 220107154-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-aminophenyl)benzamideYield 55.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxyphenyl)benzamide (232 mg), diphenylphosphoryl azide (151 mg), and triethylamine (0.084 ml) in benzene (10 ml) was refluxed for 5 hours and 1N hydrochloric acid (4 ml) was added to the solution. The mixture was refluxed for 4 hours and the mixture was washed with aqueous saturated sodium hydrogen carbonate and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give crude oil. The oil was purified by silica gel column (10 g, 2% methanol in chloroform) and the product was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-aminophenyl)benzamide (120 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe mixture was refluxed for 4 hours
  3. washthe mixture was washed with aqueous saturated sodium hydrogen carbonate and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customto give crude oil
  7. customThe oil was purified by silica gel column (10 g, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-2f9c997335ec450e8bc1bb3eff90fce0
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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