Benzenesulfonic Acid → HCID 10535374, compound

HRID 1417913Notes

Reaction equation

HRID 1417913 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[N+]=[N-].C1(S(O)(=O)=O)C=CC=CC=1.CCOC(C)=O>CO>[NH2:15][C:13]1[CH:12]=[C:7]([CH:6]=[C:5]([CH2:4][NH2:1])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 8857Ethyl AcetateHCID 19359208HCID 19359208, compound

Product 1

HCID 10535374HCID 10535374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of Methyl 3-Azidomethyl-5-nitrobenzoate (15.50 g, 65.7 mmol) and benzene sulfonic acid (22.14 g, 140 mmol) in warm methanol (320 ml) was placed in a Parr shaker bottle and purged with nitrogen for 15 minutes. Palladium on carbon catalyst (10% Pd/C, 4.0 g) was added and the shaker bottle was further purged with 7 pressurization-evacuation cycles, repressurized, and allowed to shake 18 hours, during which time the required amount of hydrogen was consumed. The catalyst was removed by filtration through a bed of Celite and the filtrate was concentrated under reduced pressure yielding a tan oil. Trituration with refluxing EtOAc (2×150 ml) followed by cooling 12 hours at -5° C. gave a tan solid which was collected by filtration, washed with EtOAc (2×50 ml) and dried under vacuum (25.82 g, 80%). 1H NMR (CD3OD): 8.25-8.23 (m, 1H), 8.07-8.06 (m, 1H), 7.86-7.80 (m, 5H), 7.49-7.42 (m, 6H), 4.29 (s, 2H), 3.97 (s, 3H).

Workup

  1. custompurged with nitrogen for 15 minutes
  2. additionPalladium on carbon catalyst (10% Pd/C, 4.0 g) was added
  3. customthe shaker bottle was further purged with 7 pressurization-evacuation cycles
  4. customthe required amount of hydrogen was consumed
  5. customThe catalyst was removed by filtration through a bed of Celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customyielding a tan oil
  8. customgave a tan solid which
  9. filtrationwas collected by filtration
  10. washwashed with EtOAc (2×50 ml)
  11. customdried under vacuum (25.82 g, 80%)

Sources & evidence

ORD record
ord-e1356fc074824b2fad8d81b54bb1d291
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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