Acetic Acid → HCID 18782722, compound

HRID 1420681Notes

Reaction equation

HRID 1420681 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([Br:10])[CH:3]=1.FC(F)(F)C(O)=O.[N-:18]=[N+:19]=[N-:20].[Na+].[C:22](O)(=O)C>C(OC(OCC)OCC)C>[Br:10][C:4]1[CH:3]=[C:2]([N:1]2[CH:22]=[N:20][N:19]=[N:18]2)[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 9610833-Bromo-4-methoxyaniline

Product 1

HCID 18782722HCID 18782722, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

4-Amino-2-bromoanisole (Desc. 4(a); 4.7 g) was dissolved in triethylorthoformate (50 ml), trifluoroacetic acid (1.8 ml) was added and the mixture heated at reflux for 48 hours. The solvent was removed in vacuo to afford a brown solid. Sodium azide (2.25 g) and acetic acid (25 ml) were added and the mixture heated at reflux for 6 hours. The product was purified on flash silica eluting with dichloromethane containing increasing proportions of methanol (0.25%, 0.5 and 0.75%) to give the title compound as a brown solid (3.98 g, 67% yield); δH (250MHz, DMSO-d6) 4.07 (3H, s, ArOCH3), 7.50 (1H, d, J 9Hz, 6-H), 8.03 (1H, dd, J 3, 9Hz, 5-H), 8.32 (1H, d, J 3Hz, 3-H), 10.16 (1H, s, 5'-H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 48 hours
  3. customThe solvent was removed in vacuo
  4. customto afford a brown solid
  5. temperaturethe mixture heated
  6. temperatureat reflux for 6 hours
  7. customThe product was purified on flash silica eluting with dichloromethane containing
  8. temperatureincreasing proportions of methanol (0.25%, 0.5 and 0.75%)

Sources & evidence

ORD record
ord-aa061b1818f24c208b8e497aaeae12d8
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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