Acetonitrile → HCID 22466766, compound

HRID 612180Notes

Reaction equation

[Li]CCCC.[CH3:6][C:7]#[N:8].CO[C:11](=[O:25])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[N:20]=[CH:21]N(C)C>C1COCC1>[CH3:19][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]2[C:13]=1[NH:20][CH:21]=[C:6]([C:7]#[N:8])[C:11]2=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To 35.0 mL of THF was added 26.6 mL (66.4 mmol) of n-BuLi solution during 5 min at -78° C. To the stirred solution was added a solution of 3.55 mL (67.9 mmol) of CH3CN in 65 mL of THF during 10 min which time the solution became white suspension, and then continued to stir for 15 min at -78° C. To the suspension was added a solution of 5.8 g (24.5 mmol) of 2-(Dimethylamino-methyleneamino)-3-methoxy-benzoic acid methyl ester in 45 mL of THF during 30 min, and then continued to stir 30 min at -78° C. during which time the mixture gradually became clear. The solution was quenched with 8.5 mL of HOAc. The resulting thick slurry was stirred and warmed to room temperature. After most of the solvent was evaporated, the residue was diluted with cold water. The separate solid was collected by filtration and washed with water. After drying in vacuo, this afforded 3.8 g of the product as an off white solid in 77.6% of yield, m.p. 270° C. (dec.), mass spectrum (electrospray, m/e): M+H 201.1

Workup

stirringto stir 30 min at -78° C. during which time the mixture gradually became clear
customThe solution was quenched with 8.5 mL of HOAc
stirringThe resulting thick slurry was stirred
temperaturewarmed to room temperature
customAfter most of the solvent was evaporated
additionthe residue was diluted with cold water
filtrationThe separate solid was collected by filtration
washwashed with water
customAfter drying in vacuo

Sources & evidence

ORD record: ord-6c2f8a3325c54ac78ca869c853834dac
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

Loading…