Acetic Anhydride → HCID 178476612, compound

HRID 1030217Notes

Reaction equation

HRID 1030217 reaction equation
[C:1]([N:3]=[C:4]([NH:6][C@@H:7]1[C:12]2[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]([CH3:20])([CH3:19])[C@H:8]1[OH:21])[CH3:5])#[N:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:21][C@H:8]1[C@H:7]([NH:6][C:4](=[N:3][C:1]#[N:2])[CH3:5])[C:12]2[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]1([CH3:20])[CH3:19])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178464619HCID 178464619, compound

Product 1

HCID 178476612HCID 178476612, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of trans-4-[N-[1-(cyanoimino)ethyl]amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (0.53 g) and acetic anhydride (0.38 g) in dry pyridine (2.65 ml) was stirred at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, successively. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was pulverized with diisopropyl ether and collected by filtration to give trans-3-acetoxy-4-[N-[1-(cyanoimino)-ethyl]amino]-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.55 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e4e8ae77e1d74fc8b3405f0c3df42d62
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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