Diethyl Ether → HCID 88776629, compound

HRID 903007Notes

Reaction equation

HRID 903007 reaction equation
C([CH:3]([C:20]([OH:22])=[O:21])[N:4]([C:10](OCC1C=CC=CC=1)=O)[CH2:5][P:6]([CH3:9])([CH3:8])=[S:7])C.[CH3:23]COCC>Br.C(O)(=O)C>[CH2:10]([N:4]([CH2:5][P:6]([CH3:9])([CH3:8])=[S:7])[CH2:3][C:20]([OH:22])=[O:21])[CH3:23]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 131711902HCID 131711902, compound

Product 1

HCID 88776629HCID 88776629, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Ethyl N-carbobenzoxy-N-(dimethylthiophosphinylmethyl)glycine (2 g., 0.005 mole) was dissolved in 36% hydrogen bromide (8 ml) in glacial acetic acid at 0° C. and the resulting mixture was stirred for one hour. Ether was added and the oily precipitate was isolated by decanting the ether layer. The oil was washed with ether twice, then suspended in benzene and treated with propylene oxide. The solution was concentrated in vacuo to yield ethyl N-(dimethylthiophosphinylmethyl)glycine (0.7 g., 0.002 mole) as an amber oil, ND22 =1.4832.

Workup

  1. customthe oily precipitate was isolated
  2. customby decanting the ether layer
  3. washThe oil was washed with ether twice
  4. additiontreated with propylene oxide
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7d83f1e7ab304908a7b8e125af2d883d
Source dataset
uspto-grants-1980_10
Patent number
US04226611

Reaction notes

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