Sulfuryl chloride → HCID 19424415, compound

HRID 743445Notes

Reaction equation

HRID 743445 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[N:11]([CH2:18][CH3:19])[S:10]2(=[O:21])=[O:20])C=CC=CC=1.S(Cl)([Cl:25])(=O)=O>C(Cl)Cl>[Cl:25][CH2:8][N:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[N:11]([CH2:18][CH3:19])[S:10]1(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194244522-Phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 19424415HCID 19424415, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (3.97 g) and sulfuryl chloride (1.47 ml) in 80 ml of methylene chloride was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in hexane. The solvent was concentrated in vacuo and the residue was purified by flash chromatography (silica gel) to afford 2.4 g (77%) of 2-chloromethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =ethyl; X'=Cl) as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane
  3. concentrationThe solvent was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-b0773af48f49443cad3b198e8b4d82dd
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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