4-Methylmorpholine → Methyl 4-[methoxy(methyl)carbamoyl]benzoate

HRID 1160856Notes

Reaction equation

HRID 1160856 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.ClC1N=C(OC)N=C([O:23][CH3:24])N=1.[CH3:25][N:26]1CCOCC1>C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:26]([O:23][CH3:24])[CH3:25])=[O:10])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 15513Monomethyl terephthalateHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazine

Product 1

HCID 54447022Methyl 4-[methoxy(methyl)carbamoyl]benzoateYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Terephthalic acid monomethyl ester (5.4 g, 30 mmol) and 2-chloro-4,6-dimethoxy-[1,3,5]triazine (7.9 g, 45 mmol) in THF (300 mL) is added N-methyl morpholine (4.95 mL, 45 mmol), the mixture is stirred at room temperature overnight. Additional N-methyl morpholine (4.95 mL, 45 mmol) is added, followed by the addition of O, N-dimethyl-hydroxylamine HCl salt (3.51 g, 45 mmol). The reaction mixture is stirred overnight, and filtered through celite. The filtrate was concentrated and purified by column chromatography on silica gel (hexane/ethyl acetate) giving the title compound (6.8 g).

Workup

  1. stirringThe reaction mixture is stirred overnight
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f1231bb547564f61aad03fae2bcbfd48
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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