Sulfuryl chloride → 2-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide

HRID 743477Notes

Reaction equation

HRID 743477 reaction equation
C1(S[CH2:8][N:9]2[S:13](=[O:15])(=[O:14])[N:12]3[CH2:16][CH2:17][CH2:18][CH:11]3[C:10]2=[O:19])C=CC=CC=1.S(Cl)([Cl:23])(=O)=O>C(Cl)Cl>[Cl:23][CH2:8][N:9]1[S:13](=[O:15])(=[O:14])[N:12]2[CH2:16][CH2:17][CH2:18][CH:11]2[C:10]1=[O:19]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 194243942-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 194244662-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (5 g) in 130 ml of methylene chloride was added sulfuryl chloride (2.02 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (2x, 150 ml, 75 ml) with stirring, the solvent decanted, and the resulting solid filtered and dried to afford 2.96 g (92%) of 2-chloromethyltetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (Formula II: R1 =H; R2 and R3 together =-(CH2)3 -; X'=Cl) as a solid, m.p. 46.5°-47.5° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated in hexane (2x, 150 ml, 75 ml)
  3. stirringwith stirring
  4. customthe solvent decanted
  5. filtrationthe resulting solid filtered
  6. customdried

Sources & evidence

ORD record
ord-58413dee0cf04deb9698f5324994e7ac
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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