Glycine ethyl ester → Ethyl N-(((Methoxy-(methylthio)phosphinyl)amino)carbonyl)glycinate

HRID 974162Notes

Reaction equation

HRID 974162 reaction equation
[P:1](=[O:9])([N:6]=[C:7]=[O:8])([S:4][CH3:5])[O:2][CH3:3].[NH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>CCOCC>[CH3:3][O:2][P:1]([NH:6][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:8])([S:4][CH3:5])=[O:9]

Participants

4

Reactant 2

HCID 12176Glycine ethyl esterHCID 14879948O,S-dimethyl phosphoroisocyanatidothioate

Product 1

HCID 15017081Ethyl N-(((Methoxy-(methylthio)phosphinyl)amino)carbonyl)glycinateYield 80.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6.1 grams (g) of O,S-dimethyl phosphoroisocyanatidothioate in 100 milliliters (ml) of ether was added dropwise with stirring 3.5 g of ethyl glycinate. A solid soon began to precipitate and after about 1 hour this was collected by filtration. The solid was recrystallized from ethanol to obtain 7.4 g of the title compound (77 percent of theory) as white crystals melting at 143°-145° C.

Workup

  1. customto precipitate and after about 1 hour
  2. filtrationthis was collected by filtration
  3. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-89dea5580eca43aca2bcfe42fb780dad
Source dataset
uspto-grants-1991_11
Patent number
US05068230

Reaction notes

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