Ethylenediamine → HCID 10617269, compound

HRID 649021Notes

Reaction equation

HRID 649021 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:21])[C:8]3[C:13]([S:14](=[O:18])(=[O:17])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[C:10]([O:19][CH3:20])[CH:9]=3)#[N:2].[CH2:22](N)[CH2:23][NH2:24].C[O-].[Na+]>CO>[NH:2]1[CH2:22][CH2:23][N:24]=[C:1]1[C:3]1[CH:16]=[C:15]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:21])[C:8]1[CH:9]=[C:10]([O:19][CH3:20])[CH:11]=[CH:12][C:13]=1[S:14]2(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 10566045HCID 10566045, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10617269HCID 10617269, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5.0 g (0.017 mol) of 3-cyano-7-methoxythioxanthen-9-one 10,10-dioxide was added ethylenediamine, 10.8 g (0.18 mol), and sodium methoxide, (0.098 g, 0.002 mol), in methanol, 70 ml, and the mixture was refluxed for 70.5 hr. The mixture was then poured into ice water, 400 ml, and the precipitate was filtered and washed with water then was recrystallized from ethanol, DMSO and H2O to provide 1.1 g of 6-(2-imidazolin-2-yl)-2-methoxythioxanthen-9-one-10,10-dioxide with m.p. 220°-224° C.; TLC on silica gel (ethanol), Rf =0.44.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customthen was recrystallized from ethanol, DMSO and H2O

Sources & evidence

ORD record
ord-79be466d06444ea3aacaffd713f82a5b
Source dataset
uspto-grants-1988_04
Patent number
US04737514

Reaction notes

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