Dichloromethane → HCID 19424400, compound

HRID 743472Notes

Reaction equation

HRID 743472 reaction equation
C1(S[CH2:8][N:9]2[C:13](=[O:14])[CH:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]([CH3:22])[S:10]2(=O)=O)C=CC=CC=1.C(Cl)[Cl:26]>>[Cl:26][CH2:8][N:9]1[C:13](=[O:14])[CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]([CH3:22])[S:10]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 19424431HCID 19424431, compound

Product 1

HCID 19424400HCID 19424400, compoundYield 92.4%

Procedure

To a solution of 2-phenylthiomethyl-4-phenylmethyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (11.78 g, 33.05 mmol) in 200 ml of methylene chloride was added in one portion under nitrogen sulfuryl chloride (3.15 ml, 39.66 mmol) and the mixture was stirred for 3.5 hours at room temperature. The mixture was concentrated in vacuo and the residue was triturated in hexane and purified by flash chromatography (20% ethyl acetate in hexane) to afford 8.82 g (92.4%) of 2-chloromethyl-4-phenylmethyl-5-methyl-1,2,5-thiadiazolidin-3-one (Formula II: R1 =H; R2 =CH2Ph; R3 =CH3 ; X'=Cl) as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated in hexane
  3. custompurified by flash chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-20b684e006fd4e0bbd58128aa4569caf
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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