Thianthrene → Thianthrene-2-sulfonic acid

HRID 1953389Notes

Reaction equation

HRID 1953389 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[S:16]([OH:19])(=[O:18])=[O:17]>ClCCl>[CH:11]1[C:12]2[S:13][C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][C:10]=1[S:16]([OH:19])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 7109ThianthreneHCID 24638Chlorosulfonic acid

Product 1

HCID 23297839Thianthrene-2-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of thianthrene (6.0 g, 27.7 mmol) in 160 mL of dichloromethane at 0° C. was added dropwise, 2.03 mL (30.5 mmol) of chlorosulfonic acid. The resulting deep purple mixture was stirred for 4 hours and then hexanes were added, and the reaction was filtered to give thianthrene-2-sulfonic acid. This acid (3.18 g, 10.7 mmol) was mixed with 7.36 g (35.3 mmol) of phosphorous pentachloride, and the neat solids were heated to a melt at 110° C. for 2 hours. The resulting mixture was quenched with ice and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated to give the title compound as a green oil which was used without further purification.

Workup

  1. filtrationthe reaction was filtered

Sources & evidence

ORD record
ord-966e3fb99daa4ff49e85fcd3ce7637bb
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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