Chlorosulfonic acid → 129949-97-9

HRID 1651508Notes

Reaction equation

HRID 1651508 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][S:8]([OH:11])(=O)=[O:9].[S:12]1[C:16]2[S:17][CH:18]=[CH:19][C:15]=2[CH:14]=[C:13]1[C:20]([O:22][CH3:23])=[O:21]>>[CH3:23][O:22][C:20]([C:13]1[S:12][C:16]2[S:17][C:18]([S:8]([Cl:7])(=[O:11])=[O:9])=[CH:19][C:15]=2[CH:14]=1)=[O:21]

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 12475296Methyl thieno[2,3-b]thiophene-2-carboxylate

Product 1

HCID 14700201129949-97-9Yield 91.2%

Procedure

Crystals of phosphorus pentachloride (9.80 g., 47.1 mmoles) were added in portions to chlorosulfonic acid (9 ml., 15.4 g., 132 mmoles) in an inert atmosphere. The solution was stirred for 15 minutes. To this solution small portions of methyl thieno[2,3-b]thiophene-2-carboxylate (8.49 g., 42.8 mmoles) were slowly added, allowing for subsiding of effervescence between additions. After the addition was complete, the solution was stirred in an inert atmosphere for 25 minutes. The resulting solution was poured carefully onto ice-water. The resulting mixture was triturated and the off-white crystals were collected and washed with water and dried in vacuo over phosphorus pentoxide to give 11.58 g of 5-methoxycarbonylthieno[2,3-b]thiophene-2-sulfonylchloride. This was used in the next step without purification.

Workup

  1. additionAfter the addition
  2. stirringthe solution was stirred in an inert atmosphere for 25 minutes
  3. additionThe resulting solution was poured carefully onto ice-water
  4. customThe resulting mixture was triturated
  5. customthe off-white crystals were collected
  6. washwashed with water
  7. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-fba3101fa34f43da9220f51ce05e8e01
Source dataset
uspto-grants-1990_05
Patent number
US04929549

Reaction notes

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