1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate

HRID 1740317Notes

Reaction equation

HRID 1740317 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])([OH:3])=O.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:3]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 11253108Methyl 3-carboxymethoxy-5-hydroxybenzoate

Product 1

HCID 21838125Methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 3-carboxymethoxy-5-hydroxybenzoate (2 g), N,N-dimethylethylenediamine (1.07 ml) and 1-hydroxybenzotriazole (1.31 g) in N,N-dimethylformamide (40 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.86 g) under ice cooling. After stirring at room temperature for 5 hours, the solvent of the reaction mixture was removed under reduced pressure. The residue was purified by column chromatography on aluminum eluting with a mixture of chloroform and methanol (20:1 to 5:1). The fractions containing the desired product were collected and evaporated in vacuo. Then the residue was triturated with diethyl ether, collected by filtration and washed with diethyl ether to give methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate (1.94 g).

Workup

  1. customthe solvent of the reaction mixture was removed under reduced pressure
  2. customThe residue was purified by column chromatography on aluminum eluting with a mixture of chloroform and methanol (20:1 to 5:1)
  3. additionThe fractions containing the desired product
  4. customwere collected
  5. customevaporated in vacuo
  6. customThen the residue was triturated with diethyl ether
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c6824011d78f4ce6929d5238ce7acd3a
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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