Water → HCID 18933332, compound

HRID 1598386Notes

Reaction equation

HRID 1598386 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH2:13][NH:14][C:15]([NH:24][CH3:25])=[C:16]([C:22]#[N:23])[C:17]([O:19]CC)=O)[CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30][N:31]=[C:32]=[S:33].O>CN(C=O)C>[C:22]([C:16]1[C:17](=[O:19])[N:31]([CH3:30])[C:32](=[S:33])[N:24]([CH3:25])[C:15]=1[NH:14][CH2:13][CH:9]1[O:10][CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=2)[CH2:8]1)#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11167Methyl isothiocyanateHCID 24758Sodium hydrideHCID 70110837HCID 70110837, compound

Product 1

HCID 18933332HCID 18933332, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 3-[4-(p-fluorobenzyl)-2-morpholinylmethylamino]-3-methylamino-2-cyanoacrylate (1.00 g, 2.66 mmol) in DMF (10 ml) was added under ice-cooling sodium hydride (0.11 g, 2.66 mmol) and the mixture was stirred for one hour. To the reaction mixture was added dropwise a solution of methyl isothiocyanate (0.19 g, 2.66 mmol) in DMF (1 ml) and the mixture was stirred under ice-cooling for 8.5 hours. Then, the reaction mixture was poured into water (30 ml) and extracted with chloroform (50 ml×4). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound from the fraction from ethyl acetate. Yield=90%.

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 8.5 hours
  3. extractionextracted with chloroform (50 ml×4)
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d7a4b6dd52bd4288aa3f995589512faa
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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