Sulfuryl chloride → HCID 19424418, compound

HRID 743440Notes

Reaction equation

HRID 743440 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH:15]([CH3:17])[CH3:16])[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]([CH:15]([CH3:17])[CH3:16])[N:11]([CH3:18])[S:10]1(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19424421HCID 19424421, compound

Product 1

HCID 19424418HCID 19424418, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-isopropyl-5-methyl -1,2,5-thiadiazolidin-3-one 1,1-dioxide (6.38 g, 23.31 mmol) in 150 ml of methylene chloride was added sulfuryl chloride (2.5 ml, 30.4 mmol) and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in hexane to afford 4.32 g (88%) of 2-chloromethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =isopropyl; R3 =methyl; X'=Cl) as a solid, m.p. 118.5°-119.5° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane

Sources & evidence

ORD record
ord-7a95544069744fd1b29d93c446cabb22
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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