Formaldehyde → HCID 19020409, compound

HRID 1087546Notes

Reaction equation

HRID 1087546 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 3mercapto-thiophene-2-carboxamide, 2.2 g of 95 percent paraformaldehyde and 13.3 g of p-toluene-sulfonic 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-7d2504f473cb4c4e9113795c7a3f6e4d
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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