Chlorosulfonic acid → 2-Thiophenesulfonyl chloride

HRID 2053063Notes

Reaction equation

HRID 2053063 reaction equation
[S:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.NC(N)=O.[Cl:10][S:11](O)(=[O:13])=[O:12]>C(Cl)Cl>[S:1]1[CH:2]=[CH:3][CH:4]=[C:5]1[S:11]([Cl:10])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86602658HCID 86602658, compound

Product 1

HCID 855182-Thiophenesulfonyl chlorideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-H-thiophene-urea (85 mg, 0.27 mmol), available from Step C of Preparative Example 16.3, was partially dissolved in methylene chloride (4 mL and added dropwise to a stirred solution of chlorosulfonic acid (0.09 mL, 1.35 mmol) in 4 mL of methylene chloride at room temperature. After 10 min, the mixture was poured into crushed ice and extracted with ethyl acetate several times. The extracts were washed with water and brine, dried with sodium sulfate, and concentrated to give the corresponding thiophene sulfonyl chloride as a greenish oil (45 mg) used in next step directly.

Workup

  1. additionthe mixture was poured
  2. custominto crushed ice
  3. extractionextracted with ethyl acetate several times
  4. washThe extracts were washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-18de5c3117d04a3a849a9e7f63158541
Source dataset
uspto-grants-2008_02
Patent number
US07326729B2

Reaction notes

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