1,1'-Carbonyldiimidazole → 2-Phenyl-ethenesulfonic acid 4-chloro-2-methoxy-benzoylamide

HRID 1272365Notes

Reaction equation

HRID 1272365 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:25]1([CH:31]=[CH:32][S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:36][S:33]([CH:32]=[CH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:34])=[O:35])=[O:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 936824-Chloro-o-anisic acidHCID 2575012-Phenylethenesulfonamide

Product 1

HCID 691163832-Phenyl-ethenesulfonic acid 4-chloro-2-methoxy-benzoylamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-2-methoxybenzoic acid (509 mg, 2.7 mmol) and CDI (443 mg, 2.7 mmol) in dichloromethane (25 ml) was heated to reflux for 30 minutes. After cooling down to room temperature 2-phenyl-ethenesulfonic acid amide (for preparation see example 1-1, steps i) and ii)) (500 mg, 2.7 mmol) and DBU (416 mg, 2.7 mmol) were added and the mixture was stirred at room temperature overnight. After washing twice with 1N HCl (50 ml each) and water (50 ml) the mixture was dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (RP18, methanol-water-gradient) returned the title compound (570 mg, 60% yield) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. additionwere added
  4. washAfter washing twice with 1N HCl (50 ml each) and water (50 ml) the mixture
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03552ad3367441da84ed33d8e0679da5
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

Loading…