1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21838182, compound

HRID 1740304Notes

Reaction equation

HRID 1740304 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]2[CH:18]=[C:17]([Cl:19])[S:16][C:15]=2[Cl:20])[CH:13]=1)[C:8]([OH:10])=O)=[O:4].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:20][C:15]1[S:16][C:17]([Cl:19])=[CH:18][C:14]=1[C:12]1[CH:11]=[C:7]([C:8](=[O:10])[NH:25][CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[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 21838083HCID 21838083, compound

Product 1

HCID 21838182HCID 21838182, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-methoxycarbonyl-5-(2,5-dichlorothiophen-3-yl)benzoic acid (0.7 g), N,N-dimethylethylenediamine (0.186 g) and 1-hydroxybenzotriazole (0.314 g) in dichloromethane (25 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.446 g) under ice cooling, and the solution was stirred for 7 hours at room temperature. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate solution with stirring. The organic layer was successively washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to afford methyl 5-(2,5-dichlorothiophen-3-yl)-3-[(2-dimethylaminoethyl)carbamoyl]benzoate (0.57 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. stirringwith stirring
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-bc7a02f2355d4f6695ca34afb8c07464
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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