Formaldehyde → HCID 21699110, compound

HRID 1597165Notes

Reaction equation

HRID 1597165 reaction equation
[Cl:1][C:2]1[S:13][C:5]2[S:6][C:7]([S:11][CH3:12])=[CH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.Cl.C(NCC)C.C=O.[C:22](=O)([O-])[O-:23].[K+].[K+]>CO.O.C(O)(=O)C>[Cl:1][C:2]1[S:13][C:5]2[S:6][C:7]([S:11][CH3:12])=[C:8]([CH2:22][OH:23])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 10197650Diethylammonium chlorideHCID 21699026HCID 21699026, compound

Product 1

HCID 21699110HCID 21699110, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-6-methylthio-4-oxo-4H-thieno[2,3-b]thiopyran (6.64 g, 0.027 mol), diethylamine hydrochloride (19.65 g, 0.24 mol) and paraformaldehyde (17.16 g) were added to an aqueous solution of 80% acetic acid and refluxed under heating for 30 hours. The solvent was removed under reduced pressure. The residue was added with ice water and stirred for a while, and supernatant was removed. The remaining viscous matter was dissolved in dimethylformamide (150 ml), filtered for removal of the insoluble matter. Then, the filtrate was added with water (40 ml), methanol (100 ml) and potassium carbonate (37 g, 0.7 mol) and stirred for 35 minutes. Then, ice water (700 ml) was added and the resulting precipitates were collected by filtration. The precipitates were recrystallized from ethanol to obtain 3.5 g (yield: 46.5%) of 2-chloro-5-hydroxymethyl-6-methylthio-4-oxo-4H-thieno[2,3-b]thiopyran.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 30 hours
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was added with ice water
  5. customwas removed
  6. dissolutionThe remaining viscous matter was dissolved in dimethylformamide (150 ml)
  7. filtrationfiltered for removal of the insoluble matter
  8. stirringstirred for 35 minutes
  9. customthe resulting precipitates
  10. filtrationwere collected by filtration
  11. customThe precipitates were recrystallized from ethanol

Sources & evidence

ORD record
ord-42d6d1f3af644a2d8dee2cb433076124
Source dataset
uspto-grants-2001_09
Patent number
US06294527B1

Reaction notes

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