Acetonitrile → HCID 46866644, compound

HRID 879963Notes

Reaction equation

HRID 879963 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH2:19][NH:20][C:21]([P:23]([O:29]C(C)C)([O:25]C(C)C)=[O:24])=[O:22])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Br)(C)C.CC#N>C(Cl)(Cl)Cl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH2:19][NH:20][C:21]([P:23]([OH:29])([OH:25])=[O:24])=[O:22])(=[O:15])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 76113BromotrimethylsilaneHCID 46865045HCID 46865045, compound

Product 1

HCID 46866644HCID 46866644, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To the 1-[4-phenoxybenzenesulfonamido]-2-[diisopropylphophonoform amido]ethane (0.45 g, 0.93 mmol) in 10 ml CHCl3 was added TMSBr (5 eq, 0.62 ml, 4.6 mmol) and reaction was stirred and heated at 50° C. for 2.5 hours. The reaction mixture was monitored by 31P NMR. The solvent was evaporated and to the mixture reaction was added 5 ml MeOH for one hour. The solvent was evaporated to give a yellow oil. The product was solidified from MeCN to give 0.29 g (78%) a white solid, m.p.=166-169° C.

Workup

  1. customThe solvent was evaporated and to the mixture reaction
  2. additionwas added 5 ml MeOH for one hour
  3. customThe solvent was evaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-54ee2e31062c490bb41d5e140c03f91a
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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