Triethylamine → 3-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester

HRID 2426131Notes

Reaction equation

HRID 2426131 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:18]=[C:17]([OH:19])[C:16]([CH3:20])=[CH:15][CH:14]=1.C(N([CH2:26][CH3:27])CC)C.[C:28](=[O:31])(O)[O-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:20])=[C:17]([O:19][C:28](=[O:31])[C:27]2[CH:26]=[CH:9][C:10]([F:11])=[C:2]([Cl:1])[CH:3]=2)[CH:18]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 27365483-Chloro-4-fluorobenzoyl Chloride

Product 1

HCID 672127893-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-chloro-4-fluorobenzoyl chloride (21.23 g, 110 mmol, Avocado) in tetrahydrofuran (50 mL) was added to a solution of 5-amino-o-cresol (6.16 g, 50 mmol, Aldrich) and triethylamine (17.5 mL, 125 mmol, Aldrich) and tetrahydrofuran (50 mL) dropwise with magnetic stirring and cooling in an ice-water bath. When the addition was complete, the mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was then diluted with water (125 mL) and saturated aqueous sodium bicarbonate solution (125 mL). After stirring for another 30 minutes, the precipitate was collected to give crude 3-chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester as an off-white powder. (Yield 21.83 g, 101%).

Workup

  1. temperaturecooling in an ice-water bath
  2. additionWhen the addition
  3. stirringstirred for 16 hours
  4. stirringAfter stirring for another 30 minutes
  5. customthe precipitate was collected

Sources & evidence

ORD record
ord-ec286319f10f404d91183fb1810a03ff
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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