1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66667404, compound

HRID 1620338Notes

Reaction equation

HRID 1620338 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:5](O)=[O:6].[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:5]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:6]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 66667416HCID 66667416, compound

Product 1

HCID 66667404HCID 66667404, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-4-(4-chlorophenoxy)-benzoic acid (Preparation 29, 19 g, 58 mmol), methanesulfonamide (9.67 g, 102 mmol), EDCI (19.33 g, 101.5 mmol) and DMAP (12.34 g, 101.5 mmol) in DMF (200 mL) was stirred at room temperature for 16 hours. The reaction mixture was evaporated in vacuo, diluted with DCM (500 mL), washed with aqueous 1M HCl (3×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 50% petroleum ether in EtOAc to afford the title compound as a white solid (5.4 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additiondiluted with DCM (500 mL)
  3. washwashed with aqueous 1M HCl (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 50% petroleum ether in EtOAc

Sources & evidence

ORD record
ord-4f3a30b9881d42ecae260c0cf8d41b34
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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