1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 56592712, compound

HRID 2359274Notes

Reaction equation

HRID 2359274 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1.C(N=C=NCCCN(C)C)C.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32]>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH:34][S:31]([CH3:30])(=[O:33])=[O:32])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 112654344-[(2-Methoxyphenyl)thio]benzoic acid

Product 1

HCID 56592712HCID 56592712, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(2-methoxyphenylthio)benzoic acid (126 mg, 0.48 mmol), 4-dimethylaminopyridine (12.2 mg, 0.10 mmol) and 1-ethyl-3-(dimethylaminopropyl)carbodiimide (195 mg, 0.97 mmol) were dissolved in anhydrous N,N-dimethylformamide (4 mL) and stirred for 60 minutes. To this solution was added methanesulphonamide (70 mg, 0.72 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of water (10 mL) and the mixture extracted with ethyl acetate (3×10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 50 mg of a crude oil which was purified by preparative HPLC title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. customThe reaction was quenched by the addition of water (10 mL)
  3. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd96fa0cd21a4d1d927d531b3af242be
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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