Ethylamine → HCID 86736906, compound

HRID 2049144Notes

Reaction equation

HRID 2049144 reaction equation
[CH3:1][CH:2]([C:15]1([O:20][CH2:19]1)[C:16](O)=[S:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:21]([N:23](CC)CC)[CH3:22].CC(OC(=S)C1OC1)CCCCCCCCCCCC.C([NH+](CC)CC)C.ClC(OCC)=O.C(N)C>O1CCCC1>[CH2:21]([NH:23][C:16](=[S:17])[C:15]1([CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:1])[O:20][CH2:19]1)[CH3:22]

Participants

7

Reactant 5

HCID 6341EthylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86736907HCID 86736907, compoundHCID 178442839HCID 178442839, compound

Product 1

HCID 86736906HCID 86736906, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.3 g (0.001 mole) of 2-tetradecylthioglycidic acid in 10 ml of anhydrous tetrahydrofuran (THF) at 0° C. (ice-water bath) is added 1.01 g (0.001 mole) of triethylamine in a small amount of THF. The mixture is stirred at 0° C. for about 30 minutes. To the thus-formed triethylammonium 2-tetradecylthioglycidate is added 0.108 g (0.001 mole) of ethyl chloroformate in small amount of THF and the mixture is stirred at about 0° C. (ice-water bath) for about 3 hours to prepare the corresponding mixed anhydride (a ppt. of Et3NHCl is observed). A stoichiometric excess of ethylamine in THF is then added and the mixture stirred at room temperature for 16 hours. The THF solvent is concentrated to approximately 1/4 volume, water is added and the mixture extracted with ether. After drying the ether extract (Na2SO4), the solvent is removed in vacuo giving the desired product, N-ethyl-2-tetradecylthioglycidamide, in good yield.

Workup

  1. customto prepare the
  2. stirringthe mixture stirred at room temperature for 16 hours
  3. concentrationThe THF solvent is concentrated to approximately 1/4 volume, water
  4. additionis added
  5. extractionthe mixture extracted with ether
  6. dry with materialAfter drying the ether
  7. extractionextract (Na2SO4)
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3d1a91ed1c364a90b2669c559307898e
Source dataset
uspto-grants-1980_04
Patent number
US04196300

Reaction notes

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