Ethylenediamine → HCID 86739113, compound

HRID 1154056Notes

Reaction equation

HRID 1154056 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]12[C:26](=[O:27])[O:25][C:23](=O)[C:14]=1[CH2:15][CH2:16][C:17]1[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:28]([NH2:31])[CH2:29][NH2:30]>C1(C)C=CC=CC=1>[NH2:30][CH2:29][CH2:28][N:31]1[C:23](=[O:25])[C:14]2[CH2:15][CH2:16][C:17]3[C:22]([C:13]=2[C:26]1=[O:27])=[CH:21][CH:20]=[CH:19][CH:18]=3

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 1422143,4-Dihydro-1,2-naphthalenedicarboxylic anhydrideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86739113HCID 86739113, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

27.6 g of toluene-p-sulphonic acid monohydrate are added to a solution of 27.62 g (0.138 mol) of 3,4-dihydronaphthalene-1,2-dicarboxylic acid anhydride in 300 ml of toluene, followed by 8.69 g of ethylenediamine. The mixture is heated to 60° C. for 30 minutes and then refluxed for 30 minutes, removing continuously the toluene and the water as they are formed by destillation. The residue is dried under vacuo to yield 32.7 g (90.C% of theory) of N-(2'-aminoethyl)-3,4-dihydronaphthalene-1,2-dicarboximide in the form of its toluene-p-sulphonic acid salt. This salt may be purified by recrystallisation from toluene.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customremoving continuously the toluene
  3. customthe water as they are formed by destillation
  4. customThe residue is dried under vacuo

Sources & evidence

ORD record
ord-3a851c0a1ee147b58988bf521300f936
Source dataset
uspto-grants-1984_12
Patent number
US04487942

Reaction notes

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