Methanesulfonyl chloride → HCID 178426516, compound

HRID 1030221Notes

Reaction equation

HRID 1030221 reaction equation
[C:1]([N:3]=[CH:4][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]1O)#[N:2].S(Cl)(C)(=O)=O>N1C=CC=CC=1>[C:1]([N:3]=[CH:4][NH:5][C: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])[CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178431173HCID 178431173, compound

Product 1

HCID 178426516HCID 178426516, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of trans-4-[N-(cyanoiminomethyl)amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (1.08 g) in dry pyridine (5.4 ml) was added mesyl chloride (0.77 ml) under ice-water cooling. The reaction mixture was stirred for 2 hours and 20 minutes at ambient temperature and evaporated. The residue was suspended in toluene (26 ml) and thereto was added 1,8-diazabicyclo[5,4,0]undec-7-ene (0.89 ml). The reaction mixture was stirred at 70° C. for 50 minutes and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then washed with brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to a column chromatography on silica gel (28 g) and eluted with a mixture of ethyl acetate and n-hexane (1:4→1:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from 50% aqueous ethanol to give 4-[N-(cyanoiminomethyl)amino]-2,2-dimethyl-2 H-1-benzopyran-6-carbonitrile (0.38 g).

Workup

  1. customevaporated
  2. additionwas added 1,8-diazabicyclo[5,4,0]undec-7-ene (0.89 ml)
  3. stirringThe reaction mixture was stirred at 70° C. for 50 minutes
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture of ethyl acetate and n-hexane (1:4→1:1)
  10. additionThe fractions containing the object compound
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-b13390ab5b004f7fabf8d1b109ee5fed
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

Loading…