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

HRID 2396796Notes

Reaction equation

HRID 2396796 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-phenylthiomethyltetrahydropyrrolo[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 (2×, 150 ml, 75 ml) with stirring, the solvent decanted, and the resulting solid filtered and dried to afford 2.96 g (92%) of 2-chloromethyl-tetrahydropyrrolo [1,2-b]-1,2,5-thiadiazol-3 (2H) -one 1,1-dioxide (Formula II: X'=Cl; R1 =H; R2 and R3 together=--(CH2)3 --)as a solid, m.p. 46.5°-47.5° C.

Workup

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

Sources & evidence

ORD record
ord-ac9f881ab73e4b19b457785f34590293
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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