Ethylenediamine → HCID 10805055, compound

HRID 649020Notes

Reaction equation

HRID 649020 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:19])[C:8]3[C:13]([S:14](=[O:18])(=[O:17])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)#[N:2].[CH2:20](N)[CH2:21][NH2:22].C[O-].[Na+]>CO>[NH:2]1[CH2:20][CH2:21][N:22]=[C:1]1[C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:19])[C:8]3[C:13]([S:14](=[O:17])(=[O:18])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 1039579-Oxo-9H-thioxanthene-3-carbonitrile 10,10-dioxideHCID 10942334Sodium Methoxide

Product 1

HCID 10805055HCID 10805055, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 13.5 g (0.05 mol) of 3-cyanothioxanthen-9-one 10,10-dioxide was added ethylenediamine, 6.0 g (0.1 mol), and sodium methoxide, 0.5 g (0.01 mol), in 100 ml methanol and the mixture was heated at reflux for 3 days. The reaction mixture was filtered hot and the solid was washed with two 50 ml portions of methanol. The crude product was recrystallized from ethanol to yield 3-(2-imidazolin-2-yl)thioxanthen-9-one 10,10-dioxide, 11.0 g, as bright orange crystals, m.p. 241°-242° C.

Workup

  1. temperatureat reflux for 3 days
  2. filtrationThe reaction mixture was filtered hot
  3. washthe solid was washed with two 50 ml portions of methanol
  4. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-8bf694f09c6343e9b7c0e9e98fcf8f21
Source dataset
uspto-grants-1988_04
Patent number
US04737514

Reaction notes

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