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Trimethylamine → Methyl 3-[[5-bromo-2-(trifluoromethyl)benzoyl]amino]-2,4-dimethyl-benzoate

HRID 239990
Notes
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Reaction equation

HRID 239990 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.N[C:16]1(C)[CH:25]=[C:24](C)[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH2:17]1.C[N:29]([CH3:31])C.[CH3:32]CCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([NH:29][C:31]1[C:17]([CH3:32])=[C:18]([CH:23]=[CH:24][C:25]=1[CH3:16])[C:19]([O:21][CH3:22])=[O:20])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 111923Propylphosphonic anhydrideHCID 509981405-Bromo-2-trifluoromethylbenzoic acidHCID 86707353Methyl 3-amino-3,5-dimethylbenzoate

Product 1

HCID 86707375Methyl 3-[[5-bromo-2-(trifluoromethyl)benzoyl]amino]-2,4-dimethyl-benzoateYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-2-(trifluoromethyl)benzoic acid (1.0 g, 3.53 mmol) in CH2Cl2 (6 ml) at room temperature are added methyl 3-amino-3,5-dimethylbenzoate (0.44 g, 2.47 mmol, see preparation 12) and trimethylamine (1.0 ml, 7.06 mmol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 5.6 ml, 8.83 mmol) is added via syringe. After 14 hours at ambient temperature, the reaction mixture is diluted with CH2Cl2, washed with water and brine. The organic layers are combined and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 20% ethyl acetate in hexanes to give the title compound as a white solid (0.6 g, 39%).

Workup

  1. waitAfter 14 hours at ambient temperature
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-f428251c514c41e1818ff8999a0b1fdb
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes