Phosphorus pentachloride → 2-Chlorocarbonyl-6-methyl-benzo[b] thiophene-3-sulfonic acid chloride

HRID 128281Notes

Reaction equation

HRID 128281 reaction equation
[C:1]([C:4]1[S:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[C:5]=1[S:14]([O-:17])(=O)=[O:15])(O)=[O:2].[Na+].P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-:25].[Cl-:26].[Cl-].[P+3]=O>>[Cl:25][C:1]([C:4]1[S:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[C:5]=1[S:14]([Cl:26])(=[O:17])=[O:15])=[O:2]

Participants

4

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 86737645Monosodium 2-carboxy-6-methyl-benzo[b] thiophene-3-sulfonateHCID 178527001HCID 178527001, compound

Product 1

HCID 538745162-Chlorocarbonyl-6-methyl-benzo[b] thiophene-3-sulfonic acid chlorideYield 82%

Procedure

Prepared analogous to Example 1(b) from monosodium 2-carboxy-6-methyl-benzo[b] thiophene-3-sulfonate and phosphorus-(V)-chloride in the presence of phosphorus oxide trichloride with a yield of 82% of theory. The product, which crystallized upon cooling, was used in the next step without further purification.

Workup

  1. customThe product, which crystallized
  2. temperatureupon cooling
  3. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-9f28a53b1eba47459e14931769153081
Source dataset
uspto-grants-1981_03
Patent number
US04259336

Reaction notes

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