N-(2-Hydroxyethyl)ethylenediamine → HCID 18958566, compound

HRID 1708333Notes

Reaction equation

HRID 1708333 reaction equation
Cl[CH2:2][C:3]([NH:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH:12][C:13](=[O:16])[CH2:14]Cl)=[O:4].[NH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[O:16]=[C:13]1[CH2:14][NH:17][CH2:18][CH2:19][N:20]([CH2:21][CH2:22][OH:23])[CH2:2][C:3](=[O:4])[NH:5][CH:6]2[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)[NH:12]1

Participants

5

Reactant 3

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 10340Sodium Carbonate2×HCID 10061487N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane

Product 1

HCID 18958566HCID 18958566, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

Into a 5 l. erlenmeyer flask containing 5 l. of anhydrous acetonitrile was placed 17.4 g. (65 mmol.) of N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane (see Example 2), 6.8 g. (65 mmol.) of 2-(2-aminoethylamino)ethanol and 130 g. (1.23 mmol.) of sodium carbonate. The reaction mixture was heated at 82° C. under nitrogen for 50 hours. After eliminating sodium carbonate by filtration, acetonitrile was eliminated under vacuum until the volume was reduced to 500 ml. A precipitate formed immediately and the reaction mixture was stirred for several hours at room temperature. The precipitate was filtered off and was washed with a few ml. of acetonitrile and dried under vacuum. 8.2 g. of compound (A) was obtained as a white solid.

Workup

  1. additionerlenmeyer flask containing 5 l
  2. filtrationby filtration, acetonitrile
  3. customA precipitate formed immediately
  4. filtrationThe precipitate was filtered off
  5. washwas washed with a few ml
  6. dry with materialof acetonitrile and dried under vacuum

Sources & evidence

ORD record
ord-936a92054ae1404f8ef01f19d8c9060d
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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