Triethylamine → 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 1485997Notes

Reaction equation

HRID 1485997 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:44]([C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[NH:48][CH3:49])[CH3:45]>O.ClCCl>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([N:48]([C:47]1[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=1[O:44][CH3:45])[CH3:49])=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110213535-Bromo-4-chloro-2-hydroxybenzoic acid

Product 1

HCID 686025845-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamideYield 10.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4-chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR=2.60 min (method 1)

Workup

  1. customThe organic layer was separated
  2. washwashed with NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel flash column chromatography
  7. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-73752b45560249b6ad9c5638b2756bb0
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

Loading…