Trimethylsilyl iodide → HCID 18928091, compound

HRID 1079316Notes

Reaction equation

HRID 1079316 reaction equation
I[Si](C)(C)C.C([O:8][P:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[O:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[C:28](=[O:30])[CH:29]=2)=[O:23])=[CH:17][CH:16]=1)([O:11]CC)=[O:10])C>C(Cl)(Cl)(Cl)Cl>[P:9]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]2[O:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[C:28](=[O:30])[CH:29]=2)=[O:23])=[CH:19][CH:20]=1)([OH:10])([OH:11])=[O:8]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 21256228HCID 21256228, compound

Product 1

HCID 18928091HCID 18928091, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

Iodotrimethylsilane [(CH3)3SiI](3.17 g) was added at 0° C. to a mixture of N-(4-diethoxyphosphorylmethylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide (2.99 g) and carbon tetrachloride (60 ml). This mixture was stirred at 0° C. for 1 hour and then at room temperature for 15 hours, after which it was concentrated under reduced pressure. The residue was dissolved in methanol (45 ml), poured over 4N HCl and stirred at room temperature for 30 minutes. The separated crystals were collected by filtration and recrystallized from methanol to yield N-(4-phosphonomethylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide (0.22 g, 8.5%) as light yellow prisms having a melting point of 265° to 266° C.

Workup

  1. waitat room temperature for 15 hours
  2. concentrationafter which it was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (45 ml)
  4. additionpoured over 4N HCl
  5. stirringstirred at room temperature for 30 minutes
  6. filtrationThe separated crystals were collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e9d08506722e4281a91e780d604bd9a7
Source dataset
uspto-grants-1996_12
Patent number
US05580863

Reaction notes

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