Diisopropylethylamine → HCID 24773477, compound

HRID 645381Notes

Reaction equation

HRID 645381 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].C(N(C(C)C)CC)(C)C.[Cl:21][CH:22]([CH3:26])[C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH:22]([CH3:26])[C:23]([NH:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[Cl:1])=[O:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1110192-Chloropropionyl chlorideHCID 1429382,4-Dichlorophenethylamine

Product 1

HCID 24773477HCID 24773477, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2,4-dichlorophenethylamine (1.0 g, 5.3 mmol) in dichloromethane (20 mL) was treated with diisopropylethylamine (0.82 g, 6.3 mmol) and 2-chloropropionylchloride (0.67 mL, 5.3 mmol) sequentially, and stirred at 20° C. for 4 hours. The mixture was diluted with dichloromethane (50 mL), washed with 10% aqueous HCl, brine (20 mL), dried with Na2SO4 and concentrated, resulting in 1.5 g of the desired product as a brown oil. MS calculated for C11H12Cl3NO+H: 280, observed: 280.

Workup

  1. washwashed with 10% aqueous HCl, brine (20 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e0320c6ff8054af780dd08082c8a4ba0
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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