Formaldehyde → HCID 19020409, compound

HRID 477931Notes

Reaction equation

HRID 477931 reaction equation
[SH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].C=O.O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=C(C)C=C(C)C=1>[S:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:8])[NH:9][CH2:13]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 19020470HCID 19020470, compound

Product 1

HCID 19020409HCID 19020409, compound

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

(aad) 11.1 g of 3-mercapto-thiophene-2-carboxamide, 2.2 g of 95 percent paraformaldehyde and 13.3 g of p-toluenesulfonic acid monohydrate were heated together under reflux with 300 ml of mesitylene. After the reaction finished, the mixture was left to cool and the solvent was removed in vacuo. After chromatography of the residue on silica gel and recrystallization from ethyl acetate, there was obtained 2,3-dihydro-4H-thieno[2,3-e][1,3]thiazin-4-one as yellowish crystals of m.p. 153°-155°.

Workup

  1. waitthe mixture was left
  2. temperatureto cool
  3. customthe solvent was removed in vacuo
  4. customAfter chromatography of the residue on silica gel and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6aabe61baa2a4ba9a543bf1ebcfe121b
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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