1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-Pentyloxybenzamido)-4'-bromoacetophenone

HRID 2270046Notes

Reaction equation

HRID 2270046 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:5].[CH2:13]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:13]([O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=2)=[O:5])=[O:24])=[CH:26][CH:27]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 85153Benzoic acid, 4-(pentyloxy)-HCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochloride

Product 1

HCID 183310892-(4-Pentyloxybenzamido)-4'-bromoacetophenoneYield 18.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-4′-bromoacetophenone hydrochloride (8.2 g), 4-pentyloxybenzoic acid (6.8 g) and 1-hydroxybenzotriazole (4.42 g) in dichloromethane (80 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (WSCD) (6.0 ml), and stirred for 3 hours at ambient temperature. The reaction mixture was diluted with dichloromethane (800 ml), and washed with 1N hydrochloric acid, saturated sodium hydrogen carbonate aqueous solution and brine. The organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in ethyl acetate, and collected by filtration to give 2-(4-pentyloxybenzamido)-4′-bromoacetophenone (2.49 g).

Workup

  1. washwashed with 1N hydrochloric acid, saturated sodium hydrogen carbonate aqueous solution and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7f65e92f3b3b4e5cb04dfdc1f680f4aa
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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