3,5-Dinitrobenzoyl chloride → 3-(3,5-Dinitrobenzoyl)-1,3-thiazolidine-2-thione

HRID 1632249Notes

Reaction equation

HRID 1632249 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[S:16]1[CH2:20][CH2:19][NH:18][C:17]1=[S:21].C(N(CC)CC)C>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([N:18]1[CH2:19][CH2:20][S:16][C:17]1=[S:21])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 27236992-Thiazolidinethione

Product 1

HCID 132176343-(3,5-Dinitrobenzoyl)-1,3-thiazolidine-2-thioneYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 15 ml of dimethylformamide were dissolved 3,5-dinitrobenzoyl chloride (2.5 g) and 1,3-thiazolidine-2-thione (1.3 g). To the solution was added dropwise a solution of triethyl amine (1.2 g) and dimethylformamide (2 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1 hour and at room temperature for 5 hours. The reaction mixture was filtered and the solvent was removed at a reduced pressure. To the residue was added water and the insolubles were filtered off. The filtrate was washed with cold methanol and then with ether to obtain crude crystals. Recrystallization from toluene gives 2.4 g of the desired compound as yellow needle crystals (yield 76.7%).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed at a reduced pressure
  4. additionTo the residue was added water
  5. filtrationthe insolubles were filtered off
  6. washThe filtrate was washed with cold methanol
  7. customwith ether to obtain crude crystals
  8. customRecrystallization from toluene

Sources & evidence

ORD record
ord-703010360b4043f88bac8de847b9c85d
Source dataset
uspto-grants-1984_10
Patent number
US04474814

Reaction notes

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