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

HRID 743455Notes

Reaction equation

HRID 743455 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:18])([CH2:15][CH2:16][CH3:17])[N:11]([CH2:19]C)[S:10]2(=[O:22])=[O:21])C=CC=CC=1.S(Cl)([Cl:26])(=O)=O>C(Cl)Cl>[Cl:26][CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH3:18])([CH2:15][CH2:16][CH3:17])[N:11]([CH3:19])[S:10]1(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194244382-Phenylthiomethyl-4-methyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244562-Chloromethyl-4-methyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-Phenylthiomethyl-4-methyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.96 g) and sulfuryl chloride (0.28 ml) in 25 ml of dry methylene chloride was stirred for 1.75 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in 30 ml of hexane to afford 480 mg (64.5%) of 2-chloromethyl-4-methyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =propyl; R2 =CH3 ; R3 =CH3 ; X'=Cl) as a solid, m.p. 99°-100° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in 30 ml of hexane

Sources & evidence

ORD record
ord-76524a9f0a864e7cbcb2115a04f6f88b
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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