Triethylamine → 3-[4-(Methansulfonylmethyl)phenoxy]phthalonitrile

HRID 1175658Notes

Reaction equation

HRID 1175658 reaction equation
O[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:10]([C:11]#[N:12])[C:9]=2[C:16]#[N:17])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([CH2:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:10]([C:11]#[N:12])[C:9]=2[C:16]#[N:17])=[CH:5][CH:4]=1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 534394893-(4-(Hydroxymethyl)phenoxy)phthalonitrile

Product 1

HCID 112554083-[4-(Methansulfonylmethyl)phenoxy]phthalonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[4-(hydroxymethyl)phenoxy]phthalonitrile (900 mg, 3.9 mmol) prepared according to procedures described in literature, and triethylamine (0.75 ml, 5.8 mmol) in anhydrous CH2Cl2 (50 ml), kept at 0° C. under stirring and in an inert atmosphere, methylsulfonylchloride was added (0.33 ml, 4.3 mmol). The mixture was stirred at 0° C. for 1 hour, then it was diluted with CH2Cl2 (50 ml) and washed with 1% HCl solution (60 ml), then with brine (50 ml), the organic layer was dried on Na2SO4 and the solvent was evaporated. 1.1 g (93%) of the title compound were obtained as a viscous fluid that crystallized on standing.

Workup

  1. customkept at 0° C.
  2. additionwas added (0.33 ml, 4.3 mmol)
  3. washwashed with 1% HCl solution (60 ml)
  4. dry with materialwith brine (50 ml), the organic layer was dried on Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5345f7f1f41240ca92b0bb7b8d8d8715
Source dataset
uspto-grants-2010_11
Patent number
US07842682B2

Reaction notes

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