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Dimethylamine, hydrochloride → 4-Dimethylamino-3-trifluoromethyl-benzoic acid methyl ester

HRID 1041869
Notes
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Reaction equation

HRID 1041869 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.Cl.[CH3:17][NH:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N:18]([CH3:19])[CH3:17])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 15285559Methyl 4-fluoro-3-(trifluoromethyl)benzoate

Product 1

HCID 217328474-Dimethylamino-3-trifluoromethyl-benzoic acid methyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4.48 g (22.5 mmol) 4-Fluoro-3-trifluoromethyl-benzoic acid methyl ester (Rarechem) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 8 h at 60° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 12a was obtained in 72% yield (4.00 g, 16.2 mmol).

Workup

  1. customwas reduced with high vacuum rotation evaporator at 65° C
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with water
  4. extractionThe combined water phases were extracted with dichloromethane
  5. washThe combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe oily crude was purified by column chromatography

Sources & evidence

ORD record
ord-e0999219fb1046f0b2e304582432f167
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557776B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes