Ethylenediamine → HCID 88095815, compound

HRID 266651Notes

Reaction equation

HRID 266651 reaction equation
CC(C)(NC[CH2:9][CH2:10][NH:11][C:12]([CH3:18])([CH3:17])[C:13](=[N:15][OH:16])[CH3:14])C(=NN)C.[NH2:20]CCN>CO.O>[NH2:20][CH2:9][CH2:10][NH:11][C:12]([CH3:17])([CH3:18])[C:13](=[N:15][OH:16])[CH3:14]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 85434539HCID 85434539, compound

Product 1

HCID 88095815HCID 88095815, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Compound A from Example 1 (10 g, 73.8 mmol) was added dropwise to a stirred solution of 1,2-diaminoethane (25 g, 416.7 mmol) in methanol (10 mL}at 0° C. After the addition was complete, the mixture was left overnight at room temperature with stirring. Removal of the methanol in vacuo gave a light yellow oil which was dissolved in water. The pH of the solution was adjusted to about 11. The solvent was removed under vacuum, and the residue was extracted with ethyl acetate. Evaporaticn of the organic phase gave a light yellow semi-solid which on crystallization with ether gave the product as a crystalline solid. Yield: 5.89 g (50%); mp. 65°-67° C. 1H NMR {CDCl3) δ 1.22[s, 6H, C(CH3)2 ], 1.87[s, 3H, C(=N)CH3 ], 2.49(t, 2H, CH2NH2) and 2.88(m, 2H, NHCH2). MS:(M+H)+ =160.

Workup

  1. custom}at 0° C
  2. additionAfter the addition
  3. customRemoval of the methanol in vacuo
  4. customgave a light yellow oil which
  5. customThe solvent was removed under vacuum
  6. extractionthe residue was extracted with ethyl acetate
  7. customEvaporaticn of the organic phase gave a light yellow semi-solid which
  8. customon crystallization with ether

Sources & evidence

ORD record
ord-bd0c32d590334e8a874c984c81c63a78
Source dataset
uspto-grants-1997_07
Patent number
US05651954

Reaction notes

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