1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22729149, compound

HRID 460606Notes

Reaction equation

HRID 460606 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=O)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:15]([NH2:18])[C:16]#[CH:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.C(N(CC)CC)C>[CH2:15]([NH:18][C:12]([C:9]1[O:8][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=2[CH:10]=1)=[O:14])[C:16]#[CH:17]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 239041PropargylamineHCID 227289824-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 22729149HCID 22729149, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4-Methoxybenzo(b)furan-2-carboxylic acid (44.0 g) and propargylamine (12 g) were dissolved in dimethylformamide (200 ml), and WSC (48.0 g), HOBt (43.0 g) and triethylamine (50 ml) were added thereto at room temperature. The mixture was stirred for 4 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of ammonium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as yellow crystals (45.0 g).

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of ammonium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a145847391f94abd884808ee19bee760
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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