Acetic Anhydride → trans-3-acetoxy-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 704785Notes

Reaction equation

HRID 704785 reaction equation
[C:1]([N:3]=[C:4]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]1[C@@H:10]1[C:15]2[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=2[O:13][C:12]([CH3:23])([CH3:22])[C@H:11]1[OH:24])#[N:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.C(OCC)(=O)C>[C:25]([O:24][C@H:11]1[C@H:10]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[C:4]2=[N:3][C:1]#[N:2])[C:15]2[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=2[O:13][C:12]1([CH3:22])[CH3:23])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86744545trans-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 86744546trans-3-acetoxy-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.95 g) in dry pyridine (9.5 ml) was added acetic anhydride (0.68 ml) at ambient temperature. The reaction mixture was stirred for 21 hours and 20 minutes at ambient temperature and then diluted with ethyl acetate (90 ml). The resultant solution was washed successively with 10% hydrochloric acid (50 ml, 30 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml), dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diisopropyl ether, and recrystallized from ethanol to give trans-3-acetoxy-4-(2-cyanoimino-3-methylimidazolidin-1-yl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.57 g).

Workup

  1. washThe resultant solution was washed successively with 10% hydrochloric acid (50 ml, 30 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ea188e4a692c4057aed12142bac034d1
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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