Sulfuryl chloride → 2-Chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743461Notes

Reaction equation

HRID 743461 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][C:17]([CH3:20])([Cl:19])[CH3:18])[N:11]([CH3:21])[S:10]2(=[O:23])=[O:22])C=CC=CC=1.S(Cl)([Cl:27])(=O)=O>C(Cl)Cl>[Cl:27][CH2:8][N:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH2:16][C:17]([CH3:20])([Cl:19])[CH3:18])[N:11]([CH3:21])[S:10]1(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194244422-Phenylthiomethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 194244092-Chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 35.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1. 396 g, 3.82 mmol) in 30 ml of methylene chloride was added sulfuryl chloride (0.366 ml, 4.58 mmol) and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo and the residue was purified by silica column chromatography (10% ethyl acetate in hexane) to afford 410 mg (35.4%) of 2-chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =(CH2)2C(Cl) (CH3)2 ; R3 =CH3 ; X'=Cl).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a5d0e65b23b94fc281b7ef7dd56df636
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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