4-Methylmorpholine → N-Methoxy-N,3-dimethyl-4-(trifluoromethyl)benzamide

HRID 418141Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5](O)=[O:6].Cl.[CH3:16][NH:17][O:18][CH3:19].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC(OC)(C)C.CN(C=O)C>[CH3:19][O:18][N:17]([CH3:16])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:2]([CH3:1])[CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a suspension of 3-methyl-4-trifluoromethyl-benzoic acid from step 6 (14.1 g, 69.1 mmol), N,O-dimethylhydroxylamine hydrochloride (10.78 g, 111 mmol), N-methylmorpholine (12.14 mL, 111 mmol) and 4-DMAP (844 mg, 691 mmol) in DCM (230 mL) at 0° C. were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (15.98 g, 82.9 mmol) and DMF (85 mL). The mixture was warmed up to 23° C. and was stirred for 18 h under nitrogen atmosphere. The mixture was diluted with TBME, washed with water and twice brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a brown oil (16.92 g, 99%), which was used without further purification. MS (ISP) 248.0 [M+H].

Workup

washwashed with water and twice brine
dry with materialdried over Na2SO4
customRemoval of the solvent in vacuum
waitleft the title compound as a brown oil (16.92 g, 99%), which
customwas used without further purification

Sources & evidence

ORD record: ord-39a8235caf3c48a5a3d7794e794f273b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093263B2

Reaction notes

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