Pentane → HCID 19860397, compound

HRID 2072791Notes

Reaction equation

HRID 2072791 reaction equation
CCCCC.[H-].[Na+].[CH3:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[C:21]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][N:19]=[C:18]([S:26][CH3:27])[N:17]=2)[CH:12]=[CH:13][CH:14]=1.[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29]>C1COCC1>[CH3:29][CH:28]([NH:31][C:32]([NH:25][S:22]([C:21]1[C:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([CH3:8])[CH:10]=2)=[N:17][C:18]([S:26][CH3:27])=[N:19][CH:20]=1)(=[O:23])=[O:24])=[O:33])[CH3:30]

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 61277Isopropyl isocyanate2×HCID 19860400HCID 19860400, compound

Product 1

HCID 19860397HCID 19860397, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pentane washed sodium hydride (3.99 mmol, 1.05 eq) was suspended in THF (50 mL), and 4-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinesulfonamide (1.18 g, 3.90 mm) was added slowly as a solid. The mixture was stirred for 90 minutes and isopropyl isocyanate (0.39 mL, 3.99 mmol, 1.05 eq) was added. After stirring 45 minutes an additional 0.1 mL of isopropyl isocyanate was added to complete the reaction. The THF was removed under reduced pressure and the residue was dissolved in dilute sodium hydroxide. Acetic acid was added until a pH of 4 and the aqueous solution was extracted with four 50 mL portions of ethyl acetate. The organic portions were combined, dried (Na2SO4), filtered and the solvent removed under reduced pressure to yield 1.61 g of crude solid. The crude solid was crystallized from ethanol and water to yield 1.21 g (3.06 mmoles, 80%) of white crystals, m.p. 160°-160.5° C.

Workup

  1. additionwas added
  2. customthe reaction
  3. customThe THF was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dilute sodium hydroxide
  5. additionAcetic acid was added until a pH of 4
  6. extractionthe aqueous solution was extracted with four 50 mL portions of ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customto yield 1.61 g of crude solid
  11. customThe crude solid was crystallized from ethanol and water

Sources & evidence

ORD record
ord-44a3d05733b2482fa81c540fc45472d0
Source dataset
uspto-grants-1990_04
Patent number
US04914203

Reaction notes

Loading…