Dimethylhydantoin → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](Cl)[CH:6]=[CH:7][C:8]=1[C:9]#[N:10].COCCOCCOCCOC.[CH3:26][C:27]1([CH3:34])[NH:31][C:30](=[O:32])[NH:29][C:28]1=[O:33]>>[CH3:26][C:27]1([CH3:34])[C:28](=[O:33])[N:29]([C:5]2[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)[C:30](=[O:32])[NH:31]1Participants
Conditions
- Temperature
- -10 °C
Procedure
4.47 g of the product obtained in Stage 1 above, 11.2 ml of triglyme, 2.78 g of 5,5-dimethyl hydantoin and 1.34 g of cuprous oxide are introduced then the suspension is agitated and taken to 215° C. for 4 hours. Then it is returned to ambient temperature, followed by filtering, washing with 4.5 ml of triglyme and agitating without exceeding 25° C., 4.5 ml of 22°Be concentrated ammonium hydroxide, 26 ml of water and 4.5 ml of toluene. Agitation is carried out for 15 minutes at 20° C. then the reaction medium is cooled down to -10° C., agitation is carried out for 1 hour, followed by separating, washing with 2.2 ml of toluene then 4.5 ml of water and drying. In this way 1.98 g of expected product (brown crystals) is obtained. M.p.=210° C.
Workup
- customis returned to ambient temperature
- filtrationby filtering
- washwashing with 4.5 ml of triglyme
- stirringagitating
- customwithout exceeding 25° C.
- waitAgitation is carried out for 15 minutes at 20° C.
- waitagitation is carried out for 1 hour
- customby separating
- washwashing with 2.2 ml of toluene
- dry with material4.5 ml of water and drying
Sources & evidence
- ORD record
- ord-b798f29a2c1a43939ec986100e2d74f2
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107488
Reaction notes
Loading…