Diisopropylamine → HCID 21841495, compound

HRID 1739558Notes

Reaction equation

HRID 1739558 reaction equation
C(N=C=NCCCN(C)C)C.[CH:12]([NH:15][CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=1>ClCCl>[CH:12]([N:15]([CH:16]([CH3:18])[CH3:17])[C:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 21841495HCID 21841495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.21 g of 1-ethyl 3-(3-dimethylamino-propyl)-carbodiimide (EDAC) and 3.08 ml of diisopropylamine were added to a solution of 4.3 g of 4-bromo-benzeneacetic acid (BrPhCH2COOH) in 15 ml of dichloromethane and the mixture was stirred for 10 minutes at ambient temperature. After evaporation under reduced pressure, the crude product was chromatographed on silica, eluting with an ethyl acetate/cyclohexane mixture (2/8) to obtain 3.7 g of product in the form of an oil with a Rf=0.21 ethyl acetate/cyclohexane 2/8).

Workup

  1. customAfter evaporation under reduced pressure
  2. customthe crude product was chromatographed on silica
  3. washeluting with an ethyl acetate/cyclohexane mixture (2/8)

Sources & evidence

ORD record
ord-b5c5a451597b44e8ba3668555aaca625
Source dataset
uspto-grants-1999_10
Patent number
US05965763

Reaction notes

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