Formaldehyde → 3-[(Dimethylamino)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

HRID 1086516Notes

Reaction equation

HRID 1086516 reaction equation
[O:1]=[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[S:5][CH2:4][CH2:3]1.Cl.[CH3:16][NH:17][CH3:18].[CH2:19]=O>C(O)(=O)C>[CH3:16][N:17]([CH2:19][CH:3]1[CH2:4][S:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[C:2]1=[O:1])=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:18]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 129347822,3-Dihydrothiopyrano[2,3-b]indol-4(9H)-one

Product 1

HCID 198261533-[(Dimethylamino)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.10 g (0.2 mol) of 4-oxo-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole, 3.26 g (0.04 mol) of dimethylamine hydrochloride and 1 g of paraformaldehyde in 50 ml of acetic acid is stirred vigorously at 100° C. under a nitrogen atmosphere and for 45 minutes. After the mixture is cooled, the solvent is evaporated off, the residue is dissolved in 80 ml of water and the aqueous phase is washed with ethyl acetate and alkalinized with concentrated ammonia solution. The precipitate is extracted with methylene chloride and the solution is washed with water saturated with sodium chloride and then concentrated. The residue is dissolved in 50 ml of hot ethanol and the solution is treated at 40° C. with 7 ml of an ethanolic solution of hydrochloric acid. After dilution with ethyl ether, the precipitate is drained, washed with ethyl ether, dried and recrystallized in ethanol.

Workup

  1. temperatureAfter the mixture is cooled
  2. customthe solvent is evaporated off
  3. dissolutionthe residue is dissolved in 80 ml of water
  4. washthe aqueous phase is washed with ethyl acetate
  5. extractionThe precipitate is extracted with methylene chloride
  6. washthe solution is washed with water saturated with sodium chloride
  7. concentrationconcentrated
  8. dissolutionThe residue is dissolved in 50 ml of hot ethanol
  9. additionthe solution is treated at 40° C. with 7 ml of an ethanolic solution of hydrochloric acid
  10. washwashed with ethyl ether
  11. customdried
  12. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-fbf49d6be72c415d939a1a77e98b06f1
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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