Ethanol → HCID 11687291, compound

HRID 1741277Notes

Reaction equation

HRID 1741277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[CH2:13](N(CC)CC)[CH3:14].Cl.C(N=C=NCCCN(C)C)C.N1(C2C=CN=CC=2)CCCC1.C(O)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 810582,6-Dichlorophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11687291HCID 11687291, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichlorophenyl acetic acid (6.7 g, 0.033 mol) in dichloromethane (170 ml) was added triethylamine (5.9 ml, 0.043 mol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.1 g, 0.043 mol) and 4-pyrrolidinopyridine (0.58 g, 0.004 mol). Ethanol (2.5 ml, 0.043 mol) was added dropwise and the solution stirred overnight at room temperature. After this time the mixture was washed with water (2×100 ml), 1M HCl (2×100 ml), aq. K2CO3 (sat.; 2×100 ml) and brine (100 ml). The organic phase was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica, using petrol:ether (10:1) as the eluant, to give the ester (7.2 g, 94%) as a colourless oil which solidified on standing at 0° C. 1H NMR (360 MHz, d6 -DMSO) δ 1.26 (3H, t, J=7.1 Hz), 4.01 (2H, s), 4.18 (2H, q, J=7.1 Hz), 7.15 (1H, t, J=8.6 Hz), 7.32 (2H, d, J=8.6 Hz).

Workup

  1. washAfter this time the mixture was washed with water (2×100 ml), 1M HCl (2×100 ml), aq. K2CO3 (sat.; 2×100 ml) and brine (100 ml)
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-f24831eb3c9548cf915cc7d1780bcf72
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

Loading…