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

HRID 1736319Notes

Reaction equation

HRID 1736319 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[NH:11][S:10]2(=[O:19])=[O:18])C=CC=CC=1.S(Cl)([Cl:23])(=O)=O>C(Cl)Cl>[Cl:23][CH2:8][N:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][CH3:17])[NH:11][S:10]1(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244252-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.23 g, 17.43 mmol) in 200 ml of methylene chloride was added sulfuryl chloride (2.15 ml, 26.07 mmol) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (200ml) for 2 hours, and the resulting solid was filtered and dried to afford 3.54 g (90%) of 2-chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =H; X=Cl) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane (200ml) for 2 hours
  3. filtrationthe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-6e28270d6b424a4e88823971ad0d9d0c
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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