Sulfuryl chloride → 2-Chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743435Notes

Reaction equation

HRID 743435 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[N:11]([CH3:18])[S:10]2(=[O:20])=[O:19])C=CC=CC=1.S(Cl)([Cl:24])(=O)=O>C(Cl)Cl>[Cl:24][CH2:8][N:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[N:11]([CH3:18])[S:10]1(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194244492-Phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 158374782-Chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.4 g) in 150 ml of methylene chloride was added sulfuryl chloride (3.22 ml) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in hexane (150 ml) for 2 hours. The solvent was concentrated in vacuo and the residue was purified by falsh chromatography (silica gel) to afford 3.54 g of 2-chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =methyl; X'=Cl) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane (150 ml) for 2 hours
  3. concentrationThe solvent was concentrated in vacuo
  4. customthe residue was purified by falsh chromatography (silica gel)

Sources & evidence

ORD record
ord-14652091634440ea992642a0ffc64d8c
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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