p-Toluenesulfonic acid monohydrate → HCID 14601401, compound

HRID 2352280Notes

Reaction equation

HRID 2352280 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:13][C:12]2[CH:11]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[S:9][C:8]=2[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH:2]([C:6]1[S:13][C:12]2[CH:11]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[S:9][C:8]=2[CH:7]=1)=[O:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14601400HCID 14601400, compound

Product 1

HCID 14601401HCID 14601401, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(2-Dioxolanyl)thieno[3,2-b]thiophene-2-sulfonamide (10) 8.50 g (0.029 moles) was dissolved in 500 mL acetone at room temperature and 0.9 g p-toluenesulfonic acid monohydrate was added in one portion. After 5 hours at room temperature all starting material was consumed. The reaction was quenched with 125 ml saturated NaHCO3 solution and the acetone was stripped on a rotary evaporator. The resulting viscous mass was extracted with 3×300 mL ethyl acetate and these combined extracts were dried and stripped to give 6.55 g (91%) of 5-Formylthieno[3,2-b]thiophene-2-sulfonamide (11) as a tan solid, mp. 203°-204° C.

Workup

  1. customAfter 5 hours at room temperature all starting material was consumed
  2. customThe reaction was quenched with 125 ml saturated NaHCO3 solution
  3. customthe acetone was stripped on a rotary evaporator
  4. extractionThe resulting viscous mass was extracted with 3×300 mL ethyl acetate
  5. customthese combined extracts were dried

Sources & evidence

ORD record
ord-bbbda4c4cda14f07ba242de27798665b
Source dataset
uspto-grants-1989_10
Patent number
US04876271

Reaction notes

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