Sodium hydride → HCID 44315917, compound

HRID 1656469Notes

Reaction equation

HRID 1656469 reaction equation
[CH3:1][CH:2]([S:16]([NH2:19])(=[O:18])=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[H-].[Na+].[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([CH3:33])[CH3:32])[C:26]=1[N:34]=[C:35]=[O:36])([CH3:24])[CH3:23]>CN(C=O)C>[CH3:24][CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]([CH3:32])[CH3:33])[C:26]=1[NH:34][C:35]([NH:19][S:16]([CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:1])(=[O:18])=[O:17])=[O:36])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 922592,6-Diisopropylphenyl isocyanateHCID 21225990HCID 21225990, compound

Product 1

HCID 44315917HCID 44315917, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-pentadecylsulfonamide (2.91 g, 10 mmoles) in DMF (40 mL dried over 3 Å sieves) was added dropwise to a stirred, 0° C. suspension of NaH (0.5 g, 21 mmoles of hexane washed) in 10 mL dry DMF. The mixture was stirred 30 minutes at 0° C., then warmed to room temperature for 3 hours. It was then cooled back to 0° C. and a solution of 2,6-diisopropylphenylisocyanate (2.14 mL, 10 mmoles) in 10 mL DMF was added dropwise. The mixture was allowed to warm to room temperature overnight, cooled to 0° C., and quenched by dropwise addition of 1N HCl (60 mL). The mixture was partitioned between EtOAc (300 mL) and H2O (100 mL). The organic layer was further washed with brine, dried, filtered, and evaporated to provide an oil which was flash chromatographed (silica gel, 4:1 hexane-EtOAc) to produce 3 g of an oil which solidified on standing (m.p. 65°-75° C.).

Workup

  1. temperaturewarmed to room temperature for 3 hours
  2. temperatureIt was then cooled back to 0° C.
  3. temperatureto warm to room temperature overnight
  4. temperaturecooled to 0° C.
  5. customquenched by dropwise addition of 1N HCl (60 mL)
  6. customThe mixture was partitioned between EtOAc (300 mL) and H2O (100 mL)
  7. washThe organic layer was further washed with brine
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customto provide an oil which
  12. customchromatographed (silica gel, 4:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-35a33621d7b64952b24bea5877322456
Source dataset
uspto-grants-1993_10
Patent number
US05254589

Reaction notes

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