Hydrogen Sulfide → 2-(Morpholin-4-yl)ethanethioamide

HRID 358478Notes

Reaction equation

HRID 358478 reaction equation
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1.[SH2:17]>N1C=CC=CC=1>[O:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH2:16])=[S:17])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 220554-Morpholineacetonitrile

Product 1

HCID 38476342-(Morpholin-4-yl)ethanethioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A reaction mixture was prepared from 203 ml. each of triethylamine and pyridine plus 63 g. of morpholinoacetonitrile. Hydrogen sulfide was bubbled through the heated, stirred reaction mixture for about 2.5 hours. Stirring was continued overnight at ambient temperature. The next day, H2S was passed through the heated, stirred reaction mixture for an additional 1.5 hours. At this point, the solvents were evaporated in vacuo and the residue triturated with ether. The ether was discarded and the residue dissolved in ethanol. Crystalline morpholinothioacetamide formed in the above reaction precipitated and was separated by filtration. Treatment of the filtrate with alcoholic hydrogen chloride yielded morpholinothioacetamide hydrochloride melting in the range 64°-80° C. See also J.A.C.S., 72, 2804 (1950).

Workup

  1. customA reaction mixture was prepared from 203 ml
  2. customHydrogen sulfide was bubbled through the heated
  3. customreaction mixture for about 2.5 hours
  4. stirringStirring
  5. stirringstirred
  6. customreaction mixture for an additional 1.5 hours
  7. customAt this point, the solvents were evaporated in vacuo
  8. customthe residue triturated with ether
  9. dissolutionthe residue dissolved in ethanol

Sources & evidence

ORD record
ord-a7bb75664c5245558b09f8612ee5d2ae
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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