Pentane → HCID 19860378, compound

HRID 1721878Notes

Reaction equation

HRID 1721878 reaction equation
CCCCC.[H-].[Na+].[CH3:8][N:9]([CH3:28])[C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)[C:13]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:12][N:11]=1.[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30]>C1COCC1>[CH3:28][N:9]([CH3:8])[C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)[C:13]([S:24]([NH:27][C:33]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:34])(=[O:25])=[O:26])=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 61277Isopropyl isocyanate2×HCID 19860396HCID 19860396, compound

Product 1

HCID 19860378HCID 19860378, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Pentane washed sodium hydride (22.0 mmol, 2.05 eq) was suspended in THF (100 mL) and 2-(dimethylamino)-4-[(3-methylphenyl)amino]-5-pyrimidinesulfonamide (3.72 g, 10.74 mmol) was added as a powder over a 30 minute period. After 90 minutes the solidified reaction was loosened by adding more THF (30 mL) followed by adding isopropyl isocyanate (1.09 mL, 11.06 mmole, 2.05 eq). After stirring 90 minutes a small portion of isopropyl isocyanate (150 mL) was added to complete the reaction. The THF was removed under reduced pressure and the residue was dissolved in warm water (100 mL). The pH was adjusted to 4 with acetic acid and the aqueous phase was extracted with four 150 mL portions of ethyl acetate. The organic portions were combined, dried (Na2SO4), decanted and the solvent removed to yield pale yellow crystals (4.11 g, 10.43 mmol, 97%). The crude material was crystallized once from ethanol/water to yield 3.45 g (8.76 mmol, 81%) of pure product, m.p. 178.5°-179° C.

Workup

  1. customAfter 90 minutes the solidified reaction
  2. additionwas added
  3. customthe reaction
  4. customThe THF was removed under reduced pressure
  5. dissolutionthe residue was dissolved in warm water (100 mL)
  6. extractionthe aqueous phase was extracted with four 150 mL portions of ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. customdecanted
  9. customthe solvent removed

Sources & evidence

ORD record
ord-f90634b9d9da407b97044e4d89e74b37
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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