Sodium Chloride → HCID 70620416, compound

HRID 1834474Notes

Reaction equation

HRID 1834474 reaction equation
[OH:1][C:2]1([CH2:16][C:17]#[N:18])[C:15]2[S:14][CH2:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+]>CCOCC>[OH:1][C:2]1([CH2:16][CH2:17][NH2:18])[C:15]2[S:14][CH2:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 70620526HCID 70620526, compound

Product 1

HCID 70620416HCID 70620416, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

18.5 g. 9-hydroxy-9-cyanomethyl-thiaxanthene (0.07 mol) are substantially dissolved in 150 ml. ether and slowly added dropwise, with stirring and external cooling, to a suspension of 3.8 g. lithium aluminum hydride (0.1 mol) in 50 ml. ether. The reaction mixture is subsequently vigorously stirred for 2 hours at room temperature and carefully decomposed by the addition of saturated, aqueous sodium chloride solution. The precipitated precipitates of the metal hydroxides agglomerate and, in this form, can be filtered off with suction. The filter cake is thoroughly washed through with ether and from the combined ethereal filtrates one obtains, after drying with potassium carbonate, 9-hydroxy-9-(2-aminoethyl)-thiaxanthene in the form of the hydrochloride by the dropwise addition of ethereal hydrochloric acid. The yield amounts to 17.0 g. (82% of theory) of m.p. 180°. After recrystallisation from isopropanol, the yield drops to 12.5 g. (61% of theory); the melting point thereby increases to 188°.

Workup

  1. additionexternal cooling, to a suspension of 3.8 g
  2. stirringThe reaction mixture is subsequently vigorously stirred for 2 hours at room temperature
  3. customThe precipitated precipitates of the metal hydroxides agglomerate and, in this form
  4. filtrationcan be filtered off with suction
  5. washThe filter cake is thoroughly washed through with ether and from the combined ethereal filtrates one
  6. customobtains
  7. dry with materialafter drying with potassium carbonate, 9-hydroxy-9-(2-aminoethyl)-thiaxanthene in the form of the hydrochloride by the dropwise addition of ethereal hydrochloric acid
  8. customAfter recrystallisation from isopropanol
  9. temperaturethe melting point thereby increases to 188°

Sources & evidence

ORD record
ord-d6bb279640a34a688f2623f9eff0794d
Source dataset
uspto-grants-1978_01
Patent number
US04070373

Reaction notes

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