4-Methylmorpholine → N-Methoxy-N-methyl-3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzamide

HRID 1784541Notes

Reaction equation

HRID 1784541 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15])[C:8]([OH:10])=O.Cl.[CH3:21][NH:22][O:23][CH3:24].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH3:24][O:23][N:22]([CH3:21])[C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([C:14]([F:17])([F:16])[F:15])=[C:5]([O:4][CH2:3][C:2]([F:1])([F:19])[F:18])[CH:6]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86086331HCID 86086331, compound

Product 1

HCID 86602234N-Methoxy-N-methyl-3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzoic acid from step 6 (9.22 g, 32 mmol), N,O-dimethylhydroxylamine hydrochloride (5.00 g, 51 mmol), N-methylmorpholine (5.62 mL, 51 mmol) and 4-DMAP (391 mg, 3.2 mmol) in DCM (100 mL) and DMF (20 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (7.36 g, 38 mmol) and the mixture was stirred at 23° C. for 18 h. Poured onto ice cold 1 N HCl, extracted with TBME, washed with sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a brown oil (10.555 g, 100%), %), which was used without further purification. MS (EI) 331.0 [M].

Workup

  1. additionPoured onto ice cold 1 N HCl
  2. extractionextracted with TBME
  3. washwashed with sat. NaHCO3-sol
  4. dry with materialand brine, dried over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft the title compound as a brown oil (10.555 g, 100%)
  7. custom%), which was used without further purification

Sources & evidence

ORD record
ord-d0b6ad5b81f243ac9115f220090f3ec4
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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