Methylamine → HCID 178485074, compound

HRID 704788Notes

Reaction equation

HRID 704788 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].[CH3:23][NH2:24]>C(O)C>[C:1]([N:3]=[C:4]([NH:24][CH3:23])[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 2

HCID 6329MethylamineHCID 178503932HCID 178503932, compound

Product 1

HCID 178485074HCID 178485074, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of trans-4-(3-cyano-2-methyl-1-isothioureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.50 g) and 25% aqueous methylamine (10 ml) in ethanol (10 ml) was stirred under reflux for 1 hour and 10 minutes. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on silica gel (10 g) and eluted with chloroform and then a mixture of chloroform and methanol (20:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was triturated with diisopropyl ether to give trans-4-(2-cyano-3-methylguanidino)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.38 g).

Workup

  1. temperatureunder reflux for 1 hour and 10 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washeluted with chloroform
  7. additiona mixture of chloroform and methanol (20:1)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-34b85f5bcf584212a817c3faafc7f2f1
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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