Formaldehyde → 5-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride

HRID 1086849Notes

Reaction equation

HRID 1086849 reaction equation
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[CH2:11]=O.[ClH:13].[CH3:14][NH:15][CH3:16]>C(O)(=O)C>[ClH:13].[CH3:14][N:15]([CH2:11][CH:8]1[CH2:7][S:6][C:5]2[S:1][CH:2]=[CH:3][C:4]=2[C:9]1=[O:10])[CH3:16]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 110302745,6-Dihydro-4H-thieno[2,3-b]thiopyran-4-one

Product 1

HCID 126753075-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochlorideYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5,6-dihydrothieno[2,3-b]thiopyran-4-one (12.5 g, 0.074 mol), paraformaldehyde (7.5 g, 0.25 mol), dimethylamine-hydrochloride (40 g, 0.49 mol) and acetic acid (2 ml) was heated with stirring at 100° C. for 1 hour. After allowing to cool to room temperature, the solid was triturated with ethanol and the solid was collected on a filter to yield 16.3 g (83%) of the title compound. An analytical sample was prepared by crystallization from 95% ethanol and filtration through a pad of norite-ducco-supercel to yield product with mp 155°-157° C. Anal. Calc'd. for C10H13NOS2.HCl.

Workup

  1. temperaturewas heated
  2. temperatureto cool to room temperature
  3. customthe solid was triturated with ethanol
  4. customthe solid was collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-fcf8cb3c8e5647a99d5a3dbc3049efd0
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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