Methanol → HCID 68478165, compound

HRID 1893148Notes

Reaction equation

HRID 1893148 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[O:12][CH2:13][P:14](=[O:21])([O:18]CC)[O:15]CC.C[Si](I)(C)C.CO>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[O:12][CH2:13][P:14](=[O:15])([OH:21])[OH:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 86644095HCID 86644095, compound

Product 1

HCID 68478165HCID 68478165, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diethyl 2-(2-benzthiazolyl)phenoxymethylphosphonate (0.2 g, 0.53 mmol) dissolved in dry dichloromethane (2.7 ml) under an atmosphere of nitrogen was added trimethylsilyl iodide (0.31 ml). The red solution was stirred for 2 h then methanol (4.3 ml) was added. After 2 h the solvent was removed under reduced pressure and then water (3.5 ml) was added to the residue. The mixture was concentrated under reduced pressure. Water (2 ml) was added and the mixture was concentrated under reduced pressure. This was repeated four times. The residue was washed finally with water then acetone to give 2-(2-benzthiazolyl)phenoxymethylphosphonic acid (0.13 g, 77%) δH (270 MHz, DMSO) 8.43 (1H, d, J 8 Hz), 8.04 (2H, m), 7.53 (2H, m), 7.44 (2H, m), 7.21 (1H, t, J 8 Hz), 4.4 (2H, d, J 12 Hz), δP (109.7 MHz, DMSO) 14.4

Workup

  1. customAfter 2 h the solvent was removed under reduced pressure
  2. additionwater (3.5 ml) was added to the residue
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionWater (2 ml) was added
  5. concentrationthe mixture was concentrated under reduced pressure
  6. washThe residue was washed finally with water

Sources & evidence

ORD record
ord-016a5fe8a5124c17835bb78e45aedcc8
Source dataset
uspto-grants-2013_08
Patent number
US08513219B2

Reaction notes

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