Acetic Anhydride → 4-(3-acetyl-2-cyanoiminoimidazolidin-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 704802Notes

Reaction equation

[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[C: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])[CH:10]=1)#[N:2].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([N:8]1[CH2:7][CH2:6][N:5]([C:9]2[C:14]3[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=3[O:12][C:11]([CH3:22])([CH3:21])[CH:10]=2)[C:4]1=[N:3][C:1]#[N:2])(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-cyanoiminoimidazolidin-1-yl)-2,2 -dimethyl-2H-1-benzopyran-6-carbonitrile (0.59 g) and acetic anhydride (0.94 ml) in pyridine (5.9 ml) was stirred at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with 5% hydrochloric acid and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to give 4-(3-acetyl-2-cyanoiminoimidazolidin-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.41 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
customevaporated in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washwashed with 5% hydrochloric acid and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-e3cc3d47dfde46a1987b8275927380b0
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988723

Reaction notes

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