N-Benzylethylenediamine → HCID 54538472, compound

HRID 1680504Notes

Reaction equation

HRID 1680504 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:14](=[O:29])[CH:15](Br)[C:16]1[C:17]([CH:22](Br)[C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:19]=[CH:20][CH:21]=1>C1C=CC=CC=1>[CH3:26][O:25][C:23]([CH:22]1[C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]2[C:14](=[O:29])[N:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:9][CH2:10][N:11]12)=[O:24]

Participants

4

Reactant 2

HCID 77801N-BenzylethylenediamineHCID 12199269HCID 12199269, compound

Product 1

HCID 54538472HCID 54538472, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(Phenylmethyl)ethylene diamine (10.38 g) is added dropwise to a solution of α,α'-dibromo-1,2-benzenediacetic acid dimethyl ester [24 g, described by G. Cignarella and A. Vigevani, Gazz. Chim. Ital., 98, 1474 (1968)] in benzene (600 ml). The mixture is refluxed for 6 hr, cooled and filtered. The filtrate is evaporated and the residue is chromatographed on silica gel using diethyl ether-methanol (9:1). The appropriate fractions are evaporated to give isomer A (5.7 g) of the title compound, nmr (CDCl3) δ3.3(m), 3.8(s), 4.6(d), 4.92(d), 5.30(d) and 7.3-7.8(m). The eluant for the above chromatography is changed to methanol-diethyl ether (3:7) and the appropriate eluate fractions are evaporated to give isomer B (4.1 g) of the title compound, nmr (CDCl3) δ3.3(m), 3.8(s), 4.6(d), 4.92(d), 5.30(d) and 7.3-7.8(m).

Workup

  1. temperatureThe mixture is refluxed for 6 hr
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is chromatographed on silica gel
  6. customThe appropriate fractions are evaporated

Sources & evidence

ORD record
ord-7e1033a23fe14e76bdcd1232b78825fc
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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