Ammonia → HCID 13972781, compound

HRID 1722428Notes

Reaction equation

HRID 1722428 reaction equation
[Na].N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+].ClCCCS([O-])(=O)=O.[Na+].[C:33]1([P:39]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:40][CH2:41][CH2:42][S:43]([O-:46])(=[O:45])=[O:44])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Na+].[Cl-].[Na+].FC(F)(F)C(O)=O>O1CCCC1>[C:47]1([P:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:40][CH2:41][CH2:42][S:43]([OH:46])(=[O:45])=[O:44])[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

10

Reactant 8

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 236618901-Propanesulfonic acid, 3-chloro-, sodium saltHCID 23678948HCID 23678948, compound

Product 1

HCID 13972781HCID 13972781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The compound 3-(diphenylphosphino)propanesulfonic acid was produced by the following procedure. To a solution of 3.8 g of sodium in 500 ml of liquid ammonia in a stirred reaction vessel maintained at -78° C. by cooling, 21.8 g of triphenylphosphine was added. After 30 minutes, 4.3 g of ammonium chloride was added and after an additional 30 minutes, 15 g of sodium 3-chloropropanesulfonate was added. The cooling was stopped and 400 ml of tetrahydrofuran was added to the reaction mixture. After the ammonia was evaporated, the mixture was refluxed for some time and then evaporated. The residue thereby obtained was washed with hot ethanol and the product was dried in vacuo to yield a mixture of sodium 3-(diphenylphosphino)propanesulfonate and sodium chloride. The mixture was treated with aqueous trifluoroacetic acid to afford the 3-(diphenylphosphino)propanesulfonic acid.

Workup

  1. temperatureby cooling
  2. customAfter the ammonia was evaporated
  3. temperaturethe mixture was refluxed for some time
  4. customevaporated
  5. customThe residue thereby obtained
  6. washwas washed with hot ethanol
  7. customthe product was dried in vacuo
  8. customto yield

Sources & evidence

ORD record
ord-b55c7227ed544e5dadcaebc5a76f6c04
Source dataset
uspto-grants-1989_08
Patent number
US04855399

Reaction notes

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