p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1658001Notes

Reaction equation

HRID 1658001 reaction equation
C(=[N:8][CH:9]([P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])C1C=CC=CC=1.O.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(OCC)C>[NH2:8][CH:9]([P:18]([O:20][CH2:21][CH3:22])([O:23][CH2:24][CH3:25])=[O:19])[C:10]([O:12][CH2:13][C:14]([Cl:16])([Cl:17])[Cl:15])=[O:11].[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54407468trichloroethyl N-benzylidene-alpha-amino-diethylphosphonoacetate

Product 2

HCID 6101p-Toluenesulfonic acidYield 265.3%HCID 21529974Trichloroethyl alpha-amino-diethylphosphonoacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of trichloroethyl N-benzylidene-α-amino-diethylphosphonoacetate (5.69 g., 13.2 mmole) in ethyl ether (25 ml.) is added to a rapidly stirring solution of p-toluenesulfonic acid monohydrate (2.76 g., 14.5 mmole) in ethyl ether (75 ml.). A white precipitate appears immediately. The mixture is stirred for 10 minutes at room temperature, then cooled in ice. The product is collected by suction filtration, washed with cold ethyl ether, and dried in vacuo to give trichloroethyl α-aminodiethylphosphonoacetate, p-toluenesulfonate (6.03 g.) as a white powder.

Workup

  1. temperaturecooled in ice
  2. filtrationThe product is collected by suction filtration
  3. washwashed with cold ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8b5669a074844bd78201e8d398e0b43b
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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