Ethanol → HCID 178468276, compound

HRID 704789Notes

Reaction equation

HRID 704789 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#[N:2].C(N(CC)CC)C.[CH2:30]([OH:32])[CH3:31]>>[C:1]([N:3]=[C:4]([O:32][CH2:30][CH3:31])[NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#[N:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 178503932HCID 178503932, compound

Product 1

HCID 178468276HCID 178468276, compound

Procedure

A mixture of trans-4-(3-cyano-2-methyl-1-isothioureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.48 g) and triethylamine (0.635 ml) in ethanol (5.0 ml) was stirred under reflux for 7 hours. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate (15 ml), and washed successively with 5% hydrochloric acid (15 ml) and saturated aqueous solution of sodium chloride (15 ml). The organic solution was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel (17 g), eluting with a mixture of methanol and chloroform (1:50 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethanol 1.5 ml) and n-hexane (3 ml) to give trans-4-(3-cyano-2-ethyl-1-isoureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.22 g).

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (15 ml)
  4. washwashed successively with 5% hydrochloric acid (15 ml) and saturated aqueous solution of sodium chloride (15 ml)
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. washeluting with a mixture of methanol and chloroform (1:50 V/V)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from a mixture of ethanol 1.5 ml) and n-hexane (3 ml)

Sources & evidence

ORD record
ord-4a489e734faa47eca7d63c6318b8141c
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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