Phosphoric Acid → HCID 11101324, compound

HRID 372946Notes

Reaction equation

HRID 372946 reaction equation
Cl.[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:20](=[O:24])([OH:23])([OH:22])O.P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:15][CH2:16][C:17]([OH:19])([P:20]([OH:24])(=[O:22])[OH:23])[P:20]([OH:23])(=[O:24])[OH:22])[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 24387Phosphorus trichlorideHCID 67842035HCID 67842035, compound

Product 1

HCID 11101324HCID 11101324, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

12.75 g (0.0446 mol) of 3-[N-(5-phenylpentyl)-N-methylamino]-propionic acid hydrochloride are heated under reflux at 100° with 6.1 ml of 85% phosphoric acid and 30 ml of chlorobenzene, while stirring. 11.7 ml of phosphorus trichloride are then added dropwise at 100°, evolution of the gas taking place. The reaction mixture precipitates a thick mass in the course of 30 minutes. The mixture is heated at 100° for a further 3 hours and the supernatant chlorobenzene is then decanted off. The viscous mass which remains is heated at the boil under reflux with 45 ml of 9N hydrochloric acid for 3 hours, while stirring. It is filtered hot, with addition of charcoal, and the filtrate is concentrated under reduced pressure. Addition of acetone gives the crude 3-[N-(5-phenylpentyl)-N-methyl-amino]-1-hydroxypropane-1,1-diphosphonic acid, which is recrystallized from water: melting point 124°-127° (decomposition).

Workup

  1. customThe reaction mixture precipitates a thick mass in the course of 30 minutes
  2. temperatureThe mixture is heated at 100° for a further 3 hours
  3. customthe supernatant chlorobenzene is then decanted off
  4. temperatureThe viscous mass which remains is heated at the boil
  5. temperatureunder reflux with 45 ml of 9N hydrochloric acid for 3 hours
  6. stirringwhile stirring
  7. filtrationIt is filtered hot, with addition of charcoal
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. additionAddition of acetone

Sources & evidence

ORD record
ord-9a87d600ccae4d14824f0b49ffe5a656
Source dataset
uspto-grants-1992_11
Patent number
US05162310

Reaction notes

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