Dichloromethane → Methyl 4-({[2-(dimethylamino)ethyl]amino}carbonyl)benzoate

HRID 131274Notes

Reaction equation

HRID 131274 reaction equation
C[C:2]1[CH:10]=[C:9](C(Cl)=O)[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].[C:20](=[O:23])([O-])[OH:21].[Na+].[CH2:25](Cl)Cl>C(OCC)(=O)C>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:4]([C:3]1[CH:7]=[CH:8][C:9]([C:20]([O:21][CH3:25])=[O:23])=[CH:10][CH:2]=1)=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 22057046HCID 22057046, compound

Product 1

HCID 46856258Methyl 4-({[2-(dimethylamino)ethyl]amino}carbonyl)benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of mono-methyl terephthaloyl chloride (500 mg), N,N-dimethylethylenediamine (178 mg) and diisoprpylethylamine (650 mg) in methylene chloride (5.0 mL) is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and thereto is added a saturated sodium hydrogencarbonate solution. After stirring, the organic layer is separated and concentrated in vacuo. The residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=9:1) to give methyl 4-[[[2-(dimethylamino)-ethyl]amino]carbonyl]benzoate (355 mg, yield; 70%) as yellow crystals. MS (APCI) m/z: 251 [M+H]+

Workup

  1. customthe organic layer is separated
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ae869b3138164a73bcb312b10f2afbba
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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