Reaktion #53462

Reaktionsgleichung

1-[bis(4-chlorophenyl)methyl]-3-[(3-cyanophenyl)(methylsulfonyl)methylene]azetidine

acetic acid

→

1-[bis(4-chlorophenyl)methyl]-3-[(3-carbamoylphenyl)(methylsulfonyl)methylene]azetidine

Lösungsmittel

ethanol

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction medium is cooled to room temperature
2. 2
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
3. 3
   SonstigeThe oil obtained
4. 4
   Einengenthe solution is concentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   SonstigeThe residue is precipitated in 60 cm3 of ethyl ether
6. 6
   SonstigeThe solid obtained
7. 7
   Sonstigeis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 25 cm, height 40 cm) at a nitrogen pressure of 0.5 bar with dichloromethane
8. 8
   Sonstigea dichloromethane and ethanol mixture (99.5/0.5 by volume) as eluent and collecting 30 cm3 fractions
9. 9
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    SonstigeThe solid obtained
11. 11
    Sonstigeis crystallized from 15 cm3 of ethyl ether

Vorschrift

A mixture of 4.5 g of 1-[bis(4-chlorophenyl)methyl]-3-[(3-cyanophenyl)(methylsulfonyl)methylene]azetidine in 50 cm3 of acetic acid and 50 cm3 of concentrated hydrochloric acid (d=1.18) is heated at 50° C. for 20 hours. The reaction medium is cooled to room temperature and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is taken up in 100 cm3 of ethanol and then the solution is concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 60 cm3 of ethyl ether. The solid obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 25 cm, height 40 cm) at a nitrogen pressure of 0.5 bar with dichloromethane and then a dichloromethane and ethanol mixture (99.5/0.5 by volume) as eluent and collecting 30 cm3 fractions. Fractions 35 to 46 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is crystallized from 15 cm3 of ethyl ether. 0.2 g of 1-[bis(4-chlorophenyl)methyl]-3-[(3-carbamoylphenyl)(methylsulfonyl)methylene]azetidine is obtained in the form of a solid melting at 192° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 7.35 (4H, d, J=7 Hz, 4CH arom.), 7.45 (5H, d, J=7 Hz, 4CH arom. and 2 CONH2), 7.50 (2H, m, 2CH arom.), 7.85 (2H, m, 2CH arom.)].

Quelle