4-Toluenesulfonyl chloride → 3-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate

HRID 500468

Reaktionsgleichung

Reaktionsgleichung von HRID 500468
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>CC#N>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218676634-((3-Hydroxypropyl)amino)benzonitrile

Produkt 1

HCID 218676523-(4-Cyanoanilino)propyl 4-methylbenzenesulfonateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A cooled (0° C.) solution of 4-[(3-hydroxypropyl)amino]benzonitrile (from step (i) above; 17 g, 96.5 mmol) in dry MeCN (195 mL) was treated with triethylamine (9.8 g, 96.5 mmol) and then p-toluenesulfonyl chloride (20.2 g, 106 mmol). The mixture was stirred at 0° C. for 90 minutes before being concentrated in vacuo. Water (200 mL) was added to the residue, and the aqueous solution was extracted with DCM. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by crystallisation from iso-propanol to yield 24.6 g (77%) of the sub-title compound.

Aufarbeitung

  1. concentrationbefore being concentrated in vacuo
  2. additionWater (200 mL) was added to the residue
  3. extractionthe aqueous solution was extracted with DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by crystallisation from iso-propanol

Quellen und Nachweise

ORD-Eintrag
ord-e06da6fe63584a4b92e67124f919436f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772229B2

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