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

HRID 1042487Notes

Reaction equation

HRID 1042487 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)[CH2:2][CH2:3][CH3:4].[CH3:19][NH:20][O:21][CH3:22].CN1CCOCC1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CCOC(C)=O>[CH2:1]([O:5][C:6]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8]([N:20]([O:21][CH3:22])[CH3:19])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 66855761HCID 66855761, compound

Product 1

HCID 866499672-butoxy-N-methoxy-N-methyl-4-trifluoromethyl-benzamideYield 103.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Butoxy-4-trifluoromethyl-benzoic acid (687 mg) was reacted with N,O-dimethylhydroxy amine (331 mg), NMM (0.65 ml) and DMTMM (911 mg) as described above to yield the title compound (825 mg) after column chromatography (Hex/EtOAc=7.5/1).

Sources & evidence

ORD record
ord-4d0d1793ceba44db9ab3672629b06c9a
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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