1,2-Dichloroethane → N-ethyl-N-4-methoxybenzyl 2,6-dihydroxybenzamide

HRID 2227715Notes

Reaction equation

HRID 2227715 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:15]=1[C:16](O)=[O:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:16](=[O:17])[C:15]1[C:14]([OH:13])=[CH:22][CH:21]=[CH:20][C:19]=1[OH:23])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 93382,6-Dihydroxybenzoic AcidHCID 181649HOAtHCID 296018Benzenemethanamine, N-ethyl-4-methoxy-

Product 1

HCID 22328602N-ethyl-N-4-methoxybenzyl 2,6-dihydroxybenzamideYield 32.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-ethyl-4-methoxybenzyl amine (1.07 g, 6.49 mmol) in DMF (10 mL) was added 2,6-dihydroxybenzoic acid (1.0 g, 6.49 mmol) followed by HOAt (0.97 g, 7.14 mmol) and EDC (1.31 g, 6.81 mmol). After stirring overnight, the reaction was diluted with EtOAc prior to washing 3× with H2O. The combined aqueous layers were extracted once with EtOAc. The organic fractions were combined, washed once with brine, and dried over Na2SO4 prior to concentrating using a rotary evaporator. The residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent. The resulting promising impure fractions were further purified by silica gel chromatography. A total of 631 mg of the desired N-ethyl-N-4-methoxybenzyl 2,6-dihydroxybenzamide was obtained.

Workup

  1. washto washing 3× with H2O
  2. extractionThe combined aqueous layers were extracted once with EtOAc
  3. washwashed once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationto concentrating
  6. customa rotary evaporator
  7. customThe residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent
  8. customThe resulting promising impure fractions were further purified by silica gel chromatography

Sources & evidence

ORD record
ord-912ed6ca5ec44e5399b78df47c00a3c7
Source dataset
uspto-grants-2002_07
Patent number
US06414126B1

Reaction notes

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