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Toluene → 2-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]acetic acid

HRID 417806
Notes
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Reaction equation

HRID 417806 reaction equation
[SH:1][CH2:2][C:3]([O:5]C)=[O:4].[OH-].[Na+].[Cl:9][CH2:10][CH2:11][N:12]([CH2:36][CH2:37][Cl:38])[P:13]([N:29]([CH2:33][CH2:34][Cl:35])[CH2:30][CH2:31][Cl:32])(=[O:28])[O:14][CH2:15][CH2:16]OS(C1C=CC(Br)=CC=1)(=O)=O.C1(C)C=CC=CC=1>CO>[Cl:35][CH2:34][CH2:33][N:29]([P:13]([N:12]([CH2:11][CH2:10][Cl:9])[CH2:36][CH2:37][Cl:38])([O:14][CH2:15][CH2:16][S:1][CH2:2][C:3]([OH:5])=[O:4])=[O:28])[CH2:30][CH2:31][Cl:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 16907Methyl ThioglycolateHCID 179493772-(4-Bromobenzene-sulfonyloxy)ethyl tetrakis(2-chloroethyl)phosphorodiamidate

Product 1

HCID 249848682-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]acetic acid

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
4×

Procedure

Methyl 2-mercapto-acetate, 2.6 mL (28.5 mmol), was dissolved in 10 mL dry methanol, and sodium hydroxide, 2.24 mL of 25 M solution (56 mmol), and 10 mL methanol were added, followed by 2-(4-bromobenzene-sulfonyloxy)ethyl tetrakis(2-chloroethyl)phosphorodiamidate, 26 mL of 1 M solution in toluene (26 mmol) with stirring, and a further 20 mL methanol. A white precipitate formed immediately, and a further 30 mL methanol was added to enable easy stirring overnight. The solid was filtered, and an additional 2 mL of the sodium hydroxide solution added to the filtrate and stirred for 2 hours. The basic solution was washed with ethyl acetate, then hydrochloric acid added until the solution became cloudy. This solution was extracted three times with ethyl acetate, and the combined ethyl acetate extracts backwashed with water, dilute hydrochloric acid, water, and brine, and then dried over Na2SO4 and concentrated, to give 7.31 g of 2-[[2-[[bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]acetic acid as an oil that solidified on standing. The identity was verified by 1H NMR.

Workup

  1. customA white precipitate formed immediately
  2. stirringto enable easy stirring overnight
  3. filtrationThe solid was filtered
  4. additionan additional 2 mL of the sodium hydroxide solution added to the filtrate
  5. stirringstirred for 2 hours
  6. washThe basic solution was washed with ethyl acetate
  7. additionhydrochloric acid added until the solution
  8. extractionThis solution was extracted three times with ethyl acetate
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2de6bd11c51345329069c436234911be
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093231B2

Reaction notes

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