Triethylamine → HCID 67041561, compound

HRID 62718Notes

Reaction equation

HRID 62718 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:12])[C:8]=1[O:9][CH2:10][CH3:11])[NH2:5].[CH2:13](N(CC)CC)C.ClC1C=C(N[C:30]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)=[O:31])C=C(Cl)C=1O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:30]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([O:38][CH3:13])=[O:37])=[CH:34][CH:33]=2)=[O:31])[CH:6]=[C:7]([Br:12])[C:8]=1[O:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 433516973,5-Dibromo-4-ethoxyanilineHCID 670418954-(3,5-Dichloro-4-hydroxyphenylcarbamoyl)benzoic acid

Product 1

HCID 67041561HCID 67041561, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dibromo-4-ethoxyaniline (2) (100 mg, 339 μmol) was dissolved in DCM (2.5 mL) and treated with triethylamine (143 μL, 1.02 mmol). 4-(Chlorocarbonyl)benzoic acid methyl ester (3) (135 mg, 678 μmol) was added in one portion and the resultant dark orange mixture was stirred at RT for 3 h then partitioned between EtOAc and aqueous 1M HCl. The organic layer was washed successively with saturated aqueous NaHCO3, water and brine. The organic layer was then dried over MgSO4, filtered and the solvent evaporated in vacuo. The residue was triturated from Et2O and filtered. The filtered solid was washed with methanol and the washings were concentrated in vacuo to provide methyl 4-(3,5-dibromo-4-ethoxyphenylcarbamoyl)benzoate (4) (141 mg, 73%) as a pale brown solid: m/z 456 [M−H]− (ES−).

Workup

  1. customthen partitioned between EtOAc and aqueous 1M HCl
  2. washThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was triturated from Et2O
  7. filtrationfiltered
  8. washThe filtered solid was washed with methanol
  9. concentrationthe washings were concentrated in vacuo

Sources & evidence

ORD record
ord-29f88504e4be420283fd0b5c412dddbb
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

Loading…