4-Methylmorpholine → N-methoxy-N-methyl-2-ethoxy-4-trifluoromethyl-benzamide

HRID 1042457

Reaction equation

HRID 1042457 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)[CH3:2].[CH3:17][NH:18][O:19][CH3:20].CN1CCOCC1>C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].CCOC(C)=O>[CH3:20][O:19][N:18]([CH3:17])[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:4]=1[O:3][CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 224943272-Ethoxy-4-(trifluoromethyl)benzoic acid

Product 1

HCID 86649957N-methoxy-N-methyl-2-ethoxy-4-trifluoromethyl-benzamideYield 73.3%

Reagents, catalysts & solvents 2

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Ethoxy-4-trifluoromethyl-benzoic acid (1.20 g, 5.12 mmol) was reacted with N,O-dimethylhydroxy amine (609 mg), NMM (0.95 ml) and DMTMM (1.47 mg) as described above to give the title compound (1.04 g, 73%) after column chromatography (Hex/EtOAc=5/1).

Sources & evidence

ORD record
ord-e87f3b968edf49f1abde6e58e27189d8
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Linked notes

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