Acetic Anhydride → HCID 18782529, compound

HRID 1420831Notes

Reaction equation

HRID 1420831 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=1[Br:22].C(N(CC)CC)C>ClCCl>[Br:22][C:11]1[CH:12]=[C:13]([N:16]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:1](=[O:3])[CH3:2])[CH:14]=[CH:15][C:10]=1[O:9][CH3:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18782565HCID 18782565, compound

Product 1

HCID 18782529HCID 18782529, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1.26 ml, 13.4 mmol) was added to a cooled (0° C.) solution of 2-methoxy-5-(2,2,2-trifluoroethylamino)bromobenzene (Description 56, 2.1 g) and triethylamine (1.9 ml, 1.37 g, 13.4 mmol) in dichloromethane and the mixture was heated under reflux for 18 h. The mixture was cooled and the solvent was evaporated under reduced pressure. 1,2-Dichloroethane (20 ml) was added and the mixture was heated under reflux for 24 h. Further acetic anhydride (0.6 ml) and triethylamine (0.95 ml) were added and the mixture was heated under reflux for 24 h., cooled and diluted with dichloromethane (100 ml). The mixture was diluted with water (3×50 ml) and brine (50 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with ethyl acetate and the solid was collected and dried in vacuo to give the title compound as an off-white solid (1.28 g, 59%). 1H NMR (360 MHz, CDCl3) δ7.44 (1 H, d, J 2.5 Hz), 7.17 (1 H, dd, J 8.7, 2.5 Hz), 6.93 (1 H, d, J 8.7 Hz), 4.29 (2 H, q, J 8.8 Hz), 3.94 (3 H, s), and 1.90 (3 H, m), m/z (ES+) 326, 328 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. addition1,2-Dichloroethane (20 ml) was added
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 24 h
  8. additionFurther acetic anhydride (0.6 ml) and triethylamine (0.95 ml) were added
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 24 h.
  11. temperaturecooled
  12. additiondiluted with dichloromethane (100 ml)
  13. additionThe mixture was diluted with water (3×50 ml) and brine (50 ml)
  14. dry with materialdried (MgSO4)
  15. customthe solvent was evaporated under reduced pressure
  16. customThe residue was triturated with ethyl acetate
  17. customthe solid was collected
  18. customdried in vacuo

Sources & evidence

ORD record
ord-5a49e30f1e07458087d2af3594aeb652
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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