Cesium carbonate → HCID 19424441, compound

HRID 743470Notes

Reaction equation

HRID 743470 reaction equation
[Cs].[C:2]1([CH2:8][CH:9]2[NH:13][S:12](=[O:15])(=[O:14])[NH:11][C:10]2=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:23]1([S:29][CH2:30]Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:23]1([S:29][CH2:30][N:11]2[C:10](=[O:16])[CH:9]([CH2:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:13][S:12]2(=[O:15])=[O:14])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81623Chloromethyl phenyl sulphideHCID 86749821HCID 86749821, compound

Product 1

HCID 19424441HCID 19424441, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-phenylmethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt (prepared by reacting 11.43 g (50.52 mmol) of the dioxide in methanol with 8.23 g (25.26 mmol) of Cs2CO3 followed by removal of the solvent) in 150 ml of DMF was added in one portion phenylthiomethyl chloride (8.82 g, 55.57 mmol) and the mixture was heated at 80°-90° C. under nitrogen for 17 hours. The mixture was cooled and poured into 600 ml of ice/water. The reaction mixture was extracted with ethyl acetate (3x), the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residual yellow oil was purified by silica column chromatography (5%-10% ethyl acetate in hexane) to afford 16.88 g (95.9%) of 2-phenylthiomethyl-4-phenylmethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =CH2Ph; R3 =H) as an yellow oil.

Workup

  1. customprepared
  2. customfollowed by removal of the solvent) in 150 ml of DMF
  3. temperaturethe mixture was heated at 80°-90° C. under nitrogen for 17 hours
  4. temperatureThe mixture was cooled
  5. extractionThe reaction mixture was extracted with ethyl acetate (3x)
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residual yellow oil was purified by silica column chromatography (5%-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0b808ca8733f4b46810823b75a5ebdc5
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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