Ethyl Bromide → trans-4-(2-cyanoimino-3-ethylimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 704790Notes

Reaction equation

[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[C@@H:9]1[C:14]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=2[O:12][C:11]([CH3:22])([CH3:21])[C@H:10]1[OH:23])#[N:2].[CH2:24](Br)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([N:3]=[C:4]1[N:8]([CH2:24][CH3:25])[CH2:7][CH2:6][N:5]1[C@@H:9]1[C:14]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=2[O:12][C:11]([CH3:21])([CH3:22])[C@H:10]1[OH:23])#[N:2]

Participants

Conditions

Temperature: 63 °C

Procedure

A mixture of trans-4-(2-cyanoiminoimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6carbonitrile (0.78 g), ethyl bromide (1.08 g) and potassium carbonate (1.38 g) in N,N-dimethylformamide (7.8 ml) was heated for 3 hours at 63° C. The reaction mixture was poured into ice-water (50 ml), and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was recrystallized from ethanol to give trans-4-(2-cyanoimino-3-ethylimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.58 g).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-7bd395c0a6af4e31b1418eb9df6c37c0
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988723

Reaction notes

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