1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70250203, compound

HRID 850320Notes

Reaction equation

HRID 850320 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[Cl:21])[CH:13]=1)[C:8](O)=[O:9])=[O:4].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[ClH:20].[Cl:21][C:15]1[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=1[C:12]1[CH:11]=[C:7]([C:8](=[O:9])[NH:26][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])[CH:6]=[C:5]([CH:13]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 19363114HCID 19363114, compound

Product 1

HCID 70250203HCID 70250203, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-methoxycarbonyl-5-(2,5-dichlorophenyl)benzoic acid (1.0 g), N,N-dimethylethylenediamine (0.223 g) and 1-hydroxybenzotriazole (0.376 g) in N,N-dimethylformamide (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.533 g) under ice cooling, and then the solution was stirred for five hours at room temperature. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml) and adjusted to pH 10 with 6N aqueous potassium carbonate solution with stirring. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (100 ml) eluting with a mixture of chloroform and methanol (20:1). The fractions containing the desired product were collected and evaporated in vacuo. The residue was dissolved in ethanol (8 ml) and added slightly excess 4N hydrogen chloride in dioxane to afford methyl 5-(2,5-dichlorophenyl)-3-[(2-dimethylaminoethyl)carbamoyl)benzoate.hydrochloride (0.43 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml)
  3. stirringwith stirring
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (100 ml)
  8. washeluting with a mixture of chloroform and methanol (20:1)
  9. additionThe fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo
  12. dissolutionThe residue was dissolved in ethanol (8 ml)
  13. additionadded slightly excess 4N hydrogen chloride in dioxane

Sources & evidence

ORD record
ord-e08b6721e3dd4663996f8d29d8104ff5
Source dataset
uspto-grants-2000_01
Patent number
US06017917

Reaction notes

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