Ethylenediamine → HCID 10735163, compound

HRID 649024Notes

Reaction equation

HRID 649024 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:12]1[CH:11]=[C:10]([F:18])[CH:9]=[CH:8][C:7]=1[S:6]2(=[O:20])=[O:19])#[N:2].[CH2:21](N)[CH2:22][NH2:23].C[O-].[Na+]>CO>[NH:2]1[CH2:21][CH2:22][N:23]=[C:1]1[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:12]1[CH:11]=[C:10]([F:18])[CH:9]=[CH:8][C:7]=1[S:6]2(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 3301Ethylenediamine2×HCID 10589352HCID 10589352, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10735163HCID 10735163, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-cyano-2-fluorothioxanthen-9-one 10,10-dioxide, 5.2 g (0.02 mol), ethylenediamine, 1.2 g (0.02 mol), and sodium methoxide, 0.08 g (0.0015 mol), in methanol, 76 ml, was refluxed for 4 days. Additional ethylenediamine, 1.2 g (0.02 mol), was added and reflux continued for 5 days. The mixture was poured into ice and the precipitate was filtered, dried and recrystallised from ethanol, DMSO and H2O; affording 2.6 g of 6-(2-imidazolin-2-yl)-2-fluorothioxanthen-9-one 10,10-dioxide, m.p. 248°-249° C.; TLC on silica gel (triethylamine; ethanol; hexane/1:1:2), Rf =0.8.

Workup

  1. temperaturereflux
  2. additionThe mixture was poured into ice
  3. filtrationthe precipitate was filtered
  4. customdried
  5. customrecrystallised from ethanol, DMSO and H2O

Sources & evidence

ORD record
ord-fcbb321c65eb4b4fb1a90e1d03baf5bb
Source dataset
uspto-grants-1988_04
Patent number
US04737514

Reaction notes

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