4-Toluenesulfonyl chloride → 2-[5-(4-Cyanophenyl)-1-benzofuran-2-yl]ethyl 4-methylbenzenesulfonate

HRID 2416133Notes

Reaction equation

HRID 2416133 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:9][C:7]=2[CH:8]=1.C(N(CC)CC)C.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(#N)C.CN(C)C1C=CN=CC=1>[CH3:38][C:28]1[CH:33]=[CH:32][C:31]([S:34]([O:1][CH2:2][CH2:3][C:4]2[O:5][C:6]3[CH:12]=[CH:11][C:10]([C:13]4[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=4)=[CH:9][C:7]=3[CH:8]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 114824394-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]benzonitrile

Product 1

HCID 117114052-[5-(4-Cyanophenyl)-1-benzofuran-2-yl]ethyl 4-methylbenzenesulfonateYield 80.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

The product from Example 1B (2.03 kg, 7.71 mol) in acetonitrile (31.8 kg) was treated in succession with triethylamine (1.86 kg, 18.34 mol), 4-(dimethylamino)pyridine 0.10 kg, 0.87 mol), and p-toluenesulfonyl chloride (3.50 kg, 17.99 mol). After stirring at room temperature for about 5 hours, the reaction mixture was distilled to a minimum volume and treated with isopropyl alcohol (24.1 kg). The suspension was heated at about 30° C. for 1 hour, then cooled to about 5° C., filtered, and the filter cake was washed with isopropyl alcohol (5.20 kg). The solid was dried at 50° C. to provide 2.59 kg (80% yield) of the title compound. MS-DCI (M+NH4)+ m/z at 435; 1H NMR (CDCl3 at 400 MHz) δ 2.38 (s, 3H), 3.15 (t, 2H), 4.38 (t, 2H), 6.50 (s, 1H) 7.18-7.24 (m, 2H), 7.37-7.46 (m, 2H), 7.67-7.74 (m, 7H); 13C NMR (CDCl3 at 100 MHz) δ 21.9, 28.9, 67.2, 104.4, 110.3, 111.2, 118.7, 119.2, 123.0,127.5, 127.6, 129.0, 129.4, 132.2, 132.4, 133.9, 144.4, 145.7, 154.1, 154.5.

Workup

  1. distillationthe reaction mixture was distilled to a minimum volume
  2. additiontreated with isopropyl alcohol (24.1 kg)
  3. temperatureThe suspension was heated at about 30° C. for 1 hour
  4. temperaturecooled to about 5° C.
  5. filtrationfiltered
  6. washthe filter cake was washed with isopropyl alcohol (5.20 kg)
  7. customThe solid was dried at 50° C.

Sources & evidence

ORD record
ord-a0788385daa048b39a93ba2a5ff71696
Source dataset
uspto-grants-2004_11
Patent number
US06822101B2

Reaction notes

Loading…