2-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide → 2-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide

HRID 2396797Notes

Reaction equation

HRID 2396797 reaction equation
[C:1]1([N:7]2[C:11]([SH:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][N:15]1[S:19](=[O:21])(=[O:20])[N:18]2[CH2:22][CH2:23][CH2:24][CH:17]2[C:16]1=[O:25]>CN(C=O)C>[C:1]1([N:7]2[C:11]([S:12][CH2:14][N:15]3[S:19](=[O:21])(=[O:20])[N:18]4[CH2:22][CH2:23][CH2:24][CH:17]4[C:16]3=[O:25])=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 194244662-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxideHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 153405112-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxideYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The Na salt of 1-phenyl-5-mercapto-1H-tetrazole (0.57 g) was added to a solution of 2-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide (0.5 g) in DMF (10 ml) at room temperature, and the mixture was allowed to react at 60° C. for 6 hours and then cooled. The mixture was poured into ice/water containing saturated sodium bicarbonate, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was concentrated in vacuo and the residue was purified by silica gel flash chromatography (40% ethyl acetate/hexane) to afford 0.69 g of 2-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide (Formula I: R4 =1-phenyl-1H-tetrazol-5-yl; X=S; R1 =H; R2 and R3 together=--(CH2)3 --) as a solid, m.p.99.5°-100.5° C.

Workup

  1. customto react at 60° C. for 6 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. customthe residue was purified by silica gel flash chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8516351d90cd40749aa95ba4bcedb97e
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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