Formaldehyde → HCID 19020409, compound

HRID 1109579Notes

Reaction equation

HRID 1109579 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-4a01603483c14fafa1198a53952c2ac0
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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