Diisopropylamine → HCID 21841495, compound

HRID 400249Notes

Reaction equation

HRID 400249 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-fa1346e996c24c229867b60409058c8d
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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