1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 15604080, compound

HRID 1272364Notes

Reaction equation

HRID 1272364 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[C:13]1([CH:19]=[CH:20][S:21]([NH2:24])(=[O:23])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC1C=CC=CC=1OC.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][S:21](/[CH:20]=[CH:19]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:22])=[O:23])=[O:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68257o-IodoanisoleHCID 2575012-PhenylethenesulfonamideHCID 134507554-Bromo-2-methoxybenzoic acid

Product 1

HCID 15604080HCID 15604080, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-methoxy-benzoic acid (159 mg, 0.69 mmol) and 2-phenyl-ethenesulfonic acid amide (108 mg, 0.59 mmol) (which was prepared analogously to example 1-1 steps i) to iii) starting from iodoanisole) in dichloromethane (5 mL) and N,N-dimethylformamide (DMF) (2 mL) is added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (EDCI) (170 mg, 0.89 mmol) and 4-(dimethylamino)-pyridine (DMAP) (89 mg, 0.73 mmol) at RT. The mixture was stirred at RT for 20 h, and solvent removed under reduced pressure. The crude reaction mixture is partitioned between water (15 mL) and ethyl acetate (15 mL). The organic phase is separated and washed with aq. 1M HCl (4×10 mL), and the aqueous phases combined and back extracted with ethyl acetate (3×10 mL). The organic phases were combined and washed with water (15 mL), brine (2×10 mL) and dried (sodium sulfate) and concentrated in vacuo. After flash chromatography (CH2Cl2/MeOH 10:1) (E)-2-phenyl-ethenesulfonic acid 4-bromo-2-methoxy-benzoylamide can be isolated as a white solid. Yield 65 mg (24%)

Workup

  1. customsolvent removed under reduced pressure
  2. customThe crude reaction mixture
  3. customis partitioned between water (15 mL) and ethyl acetate (15 mL)
  4. customThe organic phase is separated
  5. washwashed with aq. 1M HCl (4×10 mL)
  6. extractionback extracted with ethyl acetate (3×10 mL)
  7. washwashed with water (15 mL), brine (2×10 mL)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4d6517c88084ed3a8c6a4a3aaebcbe8
Source dataset
uspto-grants-2007_04
Patent number
US07208526B2

Reaction notes

Loading…