Water → HCID 14460454, compound

HRID 330002Notes

Reaction equation

HRID 330002 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:10][C:9]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:8]=2[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH:2]([C:6]1[S:10][C:9]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:8]=2[CH:7]=1)=[O:1]

Participants

6

Reactant 4

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 14460453HCID 14460453, compound

Product 1

HCID 14460454HCID 14460454, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(2-Dioxolanyl)thieno[2,3-b]thiophene-2-sulfonamide (2.59 g, 8.89 mmol) was suspended in acetone and p-toluenesulfonic acid (2.50 g, 13.1 mmol) was added. The mixture was stirred at room temperature for one hour at which time a solution was obtained. Water (2.0 mL) was added and stirring continued for 3 hours. A saturated solution of sodium bicarbonate (30 mL) was added dropwise, followed by the slow addition of water (40 mL). The resulting solution or mixture was seeded with a few crystals of product and the acetone was evaporated in vacuo. The crystals were collected, washed with water and dried in vacuo to give 2.10 g of 5-formylthieno[2,3-b]thiophene-2-sulfonamide, m.p. 188°-189° C. This product was used in the next step without further purification.

Workup

  1. customwas obtained
  2. stirringstirring
  3. waitcontinued for 3 hours
  4. customthe acetone was evaporated in vacuo
  5. customThe crystals were collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1cc0136e9a17420aa8453615f36ed321
Source dataset
uspto-grants-1990_01
Patent number
US04894390

Reaction notes

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