Hydrogen Bromide → HCID 86737084, compound

HRID 2057500Notes

Reaction equation

HRID 2057500 reaction equation
C(OCC[CH:6]([C:31]([OH:33])=[O:32])[N:7]([CH2:18][P:19]([S:26][CH2:27][CH2:28][CH2:29][CH3:30])([S:21][CH2:22][CH2:23][CH2:24][CH3:25])=[S:20])[C:8](OCC1C=CC=CC=1)=O)C.Br.[CH2:35]([O:37][CH2:38]C)[CH3:36]>C(O)(=O)C>[CH2:35]([O:37][CH2:38][CH2:8][N:7]([CH2:18][P:19]([S:21][CH2:22][CH2:23][CH2:24][CH3:25])([S:26][CH2:27][CH2:28][CH2:29][CH3:30])=[S:20])[CH2:6][C:31]([OH:33])=[O:32])[CH3:36]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 20330653HCID 20330653, compound

Product 1

HCID 86737084HCID 86737084, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Ethoxyethyl-N-[bis(butylthio)phosphinothioylmethyl]-N-(benzyloxycarbonyl)glycine (9.2 g., 0.017 mole) was dissolved in 30 ml. of 35% hydrobromic acid in acetic acid. The reaction was stirred for approximately 6 hours. Diethyl ether was added which precipitated a viscous oil. The oil was washed three additional times with diethyl ether and then dissolved in benzene. The benzene solution was treated with excess propylene oxide. The propylene oxide treated solution was concentrated in vacuo and the residue chromatographed on silica gel employing diethyl ether as an eluant to yield 2-ethoxyethyl-N-[bis(butylthio)phosphinothioylmethyl]glycine as an oil, ND25 =1.5490, which gave the following analysis.

Workup

  1. customprecipitated a viscous oil
  2. washThe oil was washed three additional times with diethyl ether
  3. dissolutiondissolved in benzene
  4. additionThe benzene solution was treated with excess propylene oxide
  5. concentrationThe propylene oxide treated solution was concentrated in vacuo
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-9dd3350a34614e548e3e45c9fb8224ab
Source dataset
uspto-grants-1980_07
Patent number
US04211548

Reaction notes

Loading…