Phosphonic acid → HCID 178443265, compound

HRID 1903041Notes

Reaction equation

HRID 1903041 reaction equation
[Br-].[CH2:2]([NH+:14]=[C:15]([NH2:17])[SH:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[PH:18](=[O:21])([OH:20])[OH:19]>>[PH:18](=[O:19])([O-:21])[OH:20].[CH2:2]([NH+:14]=[C:15]([NH2:17])[SH:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 407Phosphonic acidHCID 178443262HCID 178443262, compound

Product 1

HCID 178443265HCID 178443265, compoundYield 76.7%

Conditions

Temperature
90 °C

Procedure

n-Dodecyl thiouronium bromide (about 0.0495 mole) and hydrogen phosphonic acid (about 0.15 mole) were mixed and heated at about 90° C. to remove HBr. Water was added and the mixture was filtered (a nitrogen stream was used to remove oxygen). Approximately 12.4 g of the desired n-dodecyl thiouronium hydrogen phosphonate was isolated, m.p. 119°-122° C. The compound was re-precipitated from ethanol and water. The IR data were consistent with HPO-3 as the counterion, i.e., strong bands near 1195 cm-1, 1145 cm-1, 1097 cm-1, 991 cm-1 and 927 cm-1. A sharp band was also observed at 2380 cm-1 which is characteristic of the P-H linkage.

Workup

  1. customto remove HBr
  2. additionWater was added
  3. filtrationthe mixture was filtered (a nitrogen stream
  4. customto remove oxygen)

Sources & evidence

ORD record
ord-60b82d3f4dad4e72a3ead3e85a1dbcc1
Source dataset
uspto-grants-1984_03
Patent number
US04435381

Reaction notes

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