Chloromethyl phenyl sulphide → 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide

HRID 743476Notes

Reaction equation

HRID 743476 reaction equation
[S:1]1(=[O:11])(=[O:10])[NH:5][C:4](=[O:6])[CH:3]2[CH2:7][CH2:8][CH2:9][N:2]12.[C:12]1([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18][CH2:19][N:5]2[S:1](=[O:11])(=[O:10])[N:2]3[CH2:9][CH2:8][CH2:7][CH:3]3[C:4]2=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 19424405tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 194243942-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxideYield 66%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (5.0 g, 28.4 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.76 g, 42.6 mmol) and tetrabutylammonium bromide (0.91 g). The resulting mixture was refluxed for 6 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (25%-30% ethyl acetate in hexane) to afford 5.58 g (66%) of 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide (Formula VI: R1 =H; R2 and R3 together =-(CH2 )3 -) as a solid, m.p. 90.5°-91.5° C.

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (25%-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f99a6594db8344e19282c00af4866ab1
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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