2-(Diethylamino)ethanethiol → HCID 20295352, compound

HRID 1389764Notes

Reaction equation

HRID 1389764 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][SH:8])[CH2:4][CH3:5])[CH3:2].[CH:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17](Br)[CH3:18])[CH2:13][CH2:12]1)=[O:10]>CO.[OH-].[K+]>[CH:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([S:8][CH2:7][CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH3:18])[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 2

HCID 160322-(Diethylamino)ethanethiolHCID 20295326HCID 20295326, compound

Product 1

HCID 20295352HCID 20295352, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N,N-diethylaminoethylmercaptan (4 g, 0.03 mole) in methanol (10 ml), 5 N potassium hydroxide in methanol (5 ml) was added, followed by (B) (5.5 g, 0.025 mole). The mixture was heated to 40° C. for 20 hours. After removal of the solvent in vacuo, the residue was diluted with ether (50 ml) and filtered. The filtrate was washed with two 5 ml portions of 2 N sodium hydroxide followed by water and dried. The solvent was stripped in vacuo, and the residue was chromatographed on "Florisil" (100 g), eluting with ether followed by ethyl acetate-methanol (8:2) to give (C) as a faintly yellow oil.

Workup

  1. customAfter removal of the solvent in vacuo
  2. additionthe residue was diluted with ether (50 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed with two 5 ml portions of 2 N sodium hydroxide
  5. customdried
  6. customthe residue was chromatographed on "Florisil" (100 g)
  7. washeluting with ether

Sources & evidence

ORD record
ord-bcd9f0116d5445b58903b632bc3e3107
Source dataset
uspto-grants-1981_01
Patent number
US04246262

Reaction notes

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