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

HRID 2396766Notes

Reaction equation

HRID 2396766 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 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1.1 g, 3.6 mmol) in 10 ml of methylene chloride was added sulfuryl chloride (0.44 ml, 5.5 mmol) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (50ml) for 1 hour, the resulting solid filtered and purified by silica gel flash column chromatography (20-25% of ethyl acetate in hexane) to afford 0.31 g 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, m.p. 62°-63.5° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane (50ml) for 1 hour
  3. filtrationthe resulting solid filtered
  4. custompurified by silica gel flash column chromatography (20-25% of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-62f80e750d6547ef9eb031d3c0b851f5
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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