Sodium Carbonate → N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane

HRID 1708331Notes

Reaction equation

HRID 1708331 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][CH2:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[NH:18][C:19](=[O:22])[CH2:20][Cl:21])=[O:10].[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[NH2:30]>C(#N)C>[Cl:7][CH2:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[NH:18][C:19](=[O:22])[CH2:20][Cl:21])=[O:10].[O:22]=[C:19]1[CH2:20][NH:30][CH:25]2[CH:24]([CH2:29][CH2:28][CH2:27][CH2:26]2)[NH:23][CH2:8][C:9](=[O:10])[NH:11][CH:12]2[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[NH:18]1

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 438061,2-Diaminocyclohexane, trans-HCID 10061487N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane

Product 2

HCID 10061487N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexaneHCID 53848153HCID 53848153, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane was prepared according to the procedure outlined by Saburi, M. and Yoshikawa, S., "Stereochemical studies of N-methyl-(S)-alaninatocobalt(III) complexes with chiral tetraamines. II. Cobalt(III)-N-methyl(S)- and (R)-alaninate-N,N'-bis(β-aminoethyl)-1(R), 2(R)-diaminocyclohexane systems," Bull. Chem. Soc. Jpn., 1974, 47, 1184-1189. Anhydrous sodium carbonate (250 g., 2.36 mol.) was added to a solution of 33.4 g. (125 mmol.) of N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane and 15 ml. (125 mmol.) of trans-1,2diaminocyclohexane in 3750 ml. of acetonitrile. The temperature was raised to 82° C., and the reaction mixture was violently agitated for 20 hours. At the end of the reaction, sodium carbonate was eliminated by filtration and the solvent was evaporated under vacuum. The solid residue was recrystallized from ethanol. Up to five successive batches of the desired compound were obtained after the progressive concentration of the ethanolic solution under vacuum. The yield was 9.6 g. of compound (A) as a white powder.

Workup

  1. filtrationwas eliminated by filtration
  2. customthe solvent was evaporated under vacuum
  3. customThe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2f8f515068764af3bee71f7fa6981350
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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