1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-cyanoimino-3-methylimidazolidin-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 704786Notes

Reaction equation

C(O[C@H:5]1[C@H:10]([N:11]2[CH2:15][CH2:14][N:13]([CH3:16])[C:12]2=[N:17][C:18]#[N:19])[C:9]2[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:8]=2[O:7][C:6]1([CH3:27])[CH3:26])(=O)C.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[C:18]([N:17]=[C:12]1[N:13]([CH3:16])[CH2:14][CH2:15][N:11]1[C:10]1[C:9]2[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:8]=2[O:7][C:6]([CH3:27])([CH3:26])[CH:5]=1)#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of trans-3-acetoxy-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.45 g) in toluene (9 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.23 ml), and the reaction mixture was stirred at 100° C. for 2 hours and 40 minutes. The solvent was removed under reduced pressure. The residue was poured into water (30 ml) and then extracted with ethyl acetate (45 ml). The organic layer was washed with brine (30 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give 4-(2-cyanoimino-3-methylimidazolidin-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.27 g).

Workup

customThe solvent was removed under reduced pressure
additionThe residue was poured into water (30 ml)
extractionextracted with ethyl acetate (45 ml)
washThe organic layer was washed with brine (30 ml)
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-4bfa87ebb5a34d2b9f4eab4d12ed303b
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988723

Reaction notes

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