Acetic Anhydride → HCID 178476609, compound

HRID 704782Notes

Reaction equation

HRID 704782 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].[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1.C(OCC)(=O)C>[C:24]([O:23][C@H:10]1[C@H:9]([N:5]2[CH2:6][CH2:7][NH:8][C:4]2=[N:3][C:1]#[N:2])[C:14]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=2[O:12][C:11]1([CH3:21])[CH3:22])(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178431170HCID 178431170, compound

Product 1

HCID 178476609HCID 178476609, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of trans-4-(2-cyanoiminoimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.62 g) and acetic anhydride (0.47 ml) in dry pyridine (3.1 ml) was stirred at room temperature for 3 days. The mixture was diluted with ethyl acetate (30 ml) and washed with 5% hydrochloric acid (20 ml×2), brine (20 ml), saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml), successively. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of chloroform and methanol (50:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and n-hexane to give trans-3-acetoxy-4-(2-cyanoiminoimidazolidin-1-yl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.44 g).

Workup

  1. washwashed with 5% hydrochloric acid (20 ml×2), brine (20 ml), saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. washeluted with a mixture of chloroform and methanol (50:1)
  5. additionThe fractions containing the object compound
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from a mixture of dichloromethane and n-hexane

Sources & evidence

ORD record
ord-4611cae117a3427dbf424b69b9bba672
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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