Diallylamine → HCID 12791035, compound

HRID 1155237Notes

Reaction equation

HRID 1155237 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][P:8](Cl)(Cl)=[O:9])[CH3:2].[CH2:23]([NH:26][CH2:27][CH:28]=[CH2:29])[CH:24]=[CH2:25]>C(OCC)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][P:8]([N:26]([CH2:27][CH:28]=[CH2:29])[CH2:23][CH:24]=[CH2:25])([N:26]([CH2:27][CH:28]=[CH2:29])[CH2:23][CH:24]=[CH2:25])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 31279DiallylamineHCID 12791028HCID 12791028, compound

Product 1

HCID 12791035HCID 12791035, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Freshly prepared ethyl-N-[(benzylthio)carbonyl]-N-[dichlorophosphinylmethyl]-glycinate (12 g.; 0.031 mol.) dissolved in 150 ml. of diethyl ether was added to a solution containing diallylamine (12.15 g.; 0.125 mol.) in 150 ml. of diethyl ether. The reaction mixture was stirred for 16 hours at 25° C., then filtered. The filtrate was washed with 3% ammonium hydroxide, 5% hydrochloric acid and then water. The ether layer was separated, then dried and concentrated in vacuo to yield ethyl-N-[(benzylthio)carbonyl]-N-[bis(diallylamino)phosphinylmethyl]-glycinate, hemi-hydrate (10.1 g.) as an oil (nD25 =1.5373) having the following analysis:

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 3% ammonium hydroxide, 5% hydrochloric acid
  3. customThe ether layer was separated
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4c63279fd044811af522aa356b5fb70
Source dataset
uspto-grants-1981_11
Patent number
US04300942

Reaction notes

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