N,N-Dimethylethylenediamine → HCID 68937939, compound

HRID 2199716Notes

Reaction equation

HRID 2199716 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])=[O:8])=[CH:4][C:3]=1[CH3:11]

Participants

7

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 821314-Bromo-3-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68937939HCID 68937939, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-3-methylbenzoic acid (430 mg), N,N-dimethylethylenediamine (180 mg), 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (600 mg) and 4-dimethylaminopyridine (244 mg) in dichloromethane (20 mL) was stirred at ambient temperature for 4 hours, diluted with ethyl acetate (200 mL), washed with water and brine, and dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash column chromatography with 10% ethyl acetate in ammonia saturated dichloromethane.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography with 10% ethyl acetate in ammonia saturated dichloromethane

Sources & evidence

ORD record
ord-1a2e733d9d724365864b51d5845385bf
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

Loading…