Acetic Acid → HCID 15035849, compound

HRID 1195229Notes

Reaction equation

HRID 1195229 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[CH2:10]=O.[C:12]([OH:15])(=O)[CH3:13].[S:16]1[CH2:21]C[C:19](=O)[CH2:18][CH2:17]1.[OH-].[Na+]>O.CO>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:6]1[CH2:19][CH:18]2[C:12](=[O:15])[CH:13]([CH2:21][S:16][CH2:17]2)[CH2:10]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 66173Tetrahydrothiopyran-4-oneHCID 970123-Iodobenzylamine

Product 1

HCID 15035849HCID 15035849, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 100 mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a heating mantle, a standard condenser with a N2 inlet, and two glass stoppers. A mixture containing 3-iodobenzylamine (1.19 g, 5.10 mmol), paraformaldehyde (1.22 g, 40.8 mmol), and CH3OH (30 mL) was made acidic with glacial acetic acid (0.46 g, 7.65 mmol). In one portion, 4-thianone (44, 0.59 g, 5.10 mmol) was added and the resulting mixture was heated under N2 at reflux for 21 h. Evaporation of the solvent gave a reddish oil, which was dissolved in H2O (40 mL). Basification (pH~13) of the solution by the dropwise addition of 10% NaOH resulted in the formation of a milky suspension which was extracted with ether (5×40 mL). Combined extracts were dried (Na2SO4, overnight), filtered, and concentrated to a yellow oil. Digestion of the oil occurred in Skelly B (125 mL, bp 60°-68° C.) for 30 min, and the supernatant was decanted. Further digestion of the residual material was effected in pentane (2×125 mL) for 30 min. Combined supernatant extracts were concentrated (rotary evaporator the vacuum pump, overnight, RT/0.2 mm Hg) to give 0.84 g (57.5%) of a slightly crude viscous oil (25) which was used without further purification in the next step. IR (film) cm-1 3055 (Ar C--H), 2930, 2825 (C--H), 1735 (C=O), 885, 790, 695 (C--H out of plane, meta); 1H NMR (DCCl3) δ2.72-3.18 [m, 10H, ring protons and H(1,5)], 3.51 (s, 2H, ArCH2), 7.07-7.71 (m, 4H, Ar--H); 13C NMR (DCCl3) ppm 35.05 [C(2,4)], 46.95 [C(1,5)], 58.20 [C(6,8)], 60.69 (ArCH2), 94.43, 127.98, 130.23, 136.44, 137.64, 140.63 (Ar--C), 213.00 (C=O).

Workup

  1. customA 100 mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer
  2. temperaturethe resulting mixture was heated under N2
  3. temperatureat reflux for 21 h
  4. customEvaporation of the solvent
  5. customgave a reddish oil, which
  6. customresulted in the formation of a milky suspension which
  7. extractionwas extracted with ether (5×40 mL)
  8. dry with materialCombined extracts were dried (Na2SO4, overnight)
  9. filtrationfiltered
  10. concentrationconcentrated to a yellow oil
  11. customthe supernatant was decanted
  12. waitFurther digestion of the residual material was effected in pentane (2×125 mL) for 30 min
  13. concentrationwere concentrated (
  14. customrotary evaporator the vacuum pump, overnight, RT/0.2 mm Hg)

Sources & evidence

ORD record
ord-557b5eaefd504539860b0c590b468f8a
Source dataset
uspto-grants-1992_05
Patent number
US05110933

Reaction notes

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