4-Methylmorpholine → HCID 86649958, compound

HRID 1042461Notes

Reaction equation

HRID 1042461 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].[CH3:17][NH:18][O:19][CH3:20].CN1CCOCC1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C1COCC1>[CH3:20][O:19][N:18]([CH3:17])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 6420962-Nitro-4-(trifluoromethyl)benzoic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

Product 1

HCID 86649958HCID 86649958, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitro-4-trifluoromethyl-benzoic acid (2.753 mg, 11.7 mmol) in THF was reacted with N,O-dimethylhydroxy amine (1.277 g, 13.1 mmol), NMM (3 ml) and DMTMM (3.34 g) at room temperature overnight. The reaction mixture was quenched by adding H2O. The mixture was extracted with ethyl acetate (50 ml×3). The combined organic layer was washed 1M NaHCO3 (50 ml×2), 3% HCl (50 ml×2) and brine (50 ml), and then dried over MgSO4. The filterate was concentrated in vacuo to yield the title compound (2.84 g, 87%).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding H2O
  3. extractionThe mixture was extracted with ethyl acetate (50 ml×3)
  4. washThe combined organic layer was washed 1M NaHCO3 (50 ml×2), 3% HCl (50 ml×2) and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. concentrationThe filterate was concentrated in vacuo

Sources & evidence

ORD record
ord-dc3274863bd7483eb60ae0cc122336b1
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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