Sulfuric Acid → Thiophene-2-thiol, S-acetyl-

HRID 2248745Notes

Reaction equation

HRID 2248745 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.OC1[C:12](C)=[C:11]([O:14]C)[S:10]C=1C(OC)=O.S(=O)(=O)(O)O.C(O)(=S)C>C(O)(=O)C>[C:11]([S:10][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)(=[O:14])[CH3:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 72992-ChlorothiopheneHCID 54710752Methyl 3-hydroxy-4-methyl-5-methoxythiophene-2-carboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 13133366Thiophene-2-thiol, S-acetyl-Yield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The chlorothiophene of (e) above (0.016 mol) in 10 ml of acetic acid was added to a solution of 0.9 ml of concentrated sulphuric acid in 10 ml of acetic acid. Whilst stirring, thioacetic acid (0.016 mol) was added and the mixture stood at room temperature for eight hours. Filtration of the precipitate afforded 75% of acetylthiothiophene which was recrystallised from hexane, m.p. 112°-114° C.

Workup

  1. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-84c0e2b679d04790a398bf6f9fc5f9b5
Source dataset
uspto-grants-1991_08
Patent number
US05041461

Reaction notes

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