1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21997505, compound

HRID 1977300Notes

Reaction equation

HRID 1977300 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:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([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:26])=[CH:28][CH:29]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 85154p-Heptoxybenzoic acidHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochloride

Product 1

HCID 21997505HCID 21997505, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-4′-bromoacetophenone hydrochloride (5.0 g), 4-heptyloxybenzoic acid (4.72 g) and 1-hydroxybenzotriazole (2.7 g) in dichloromethane (50 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (WSCD) (3.65 ml) and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was diluted with dichloromethane (200 ml), and washed with water, 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-heptyloxybenzoylamino)-4′-bromoacetophenone (6.73 g).

Workup

  1. washwashed with water, 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-01cda527458345b098604eb199b7d2fd
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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