Hydrogen Bromide → HCID 88776074, compound

HRID 903010Notes

Reaction equation

HRID 903010 reaction equation
C([CH:3]([C:22]([OH:24])=[O:23])[N:4]([C:12](OCC1C=CC=CC=1)=O)[CH2:5][P:6]([CH2:10][CH3:11])([CH2:8][CH3:9])=[S:7])C.Br.[CH3:26]COCC>C(O)(=O)C>[CH2:12]([N:4]([CH2:5][P:6]([CH2:10][CH3:11])([CH2:8][CH3:9])=[S:7])[CH2:3][C:22]([OH:24])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 131711905HCID 131711905, compound

Product 1

HCID 88776074HCID 88776074, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl N-carbobenzoxy-N-(diethylthiophosphinylmethyl)glycine (1 g., 0.0024 mole) was dissolved in 5 ml. of 30% hydrogen bromide in glacial acetic acid at 0° C. The 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-(diethylthiophosphinylmethyl)glycine (0.15 g., 0.0005 mole) as an oil, ND25 =1.4960.

Workup

  1. customat 0° C
  2. customthe oily precipitate was isolated
  3. customby decanting the ether layer
  4. washThe oil was washed with ether twice
  5. additiontreated with propylene oxide
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-36db5ba64e4f4e819dcc95cc022581b2
Source dataset
uspto-grants-1980_10
Patent number
US04226611

Reaction notes

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