Sodium hydride → N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea

HRID 1656470Notes

Reaction equation

HRID 1656470 reaction equation
[CH2:1]([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>CN(C=O)C>[CH3:23][CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:31])[CH3:32])[C:25]=1[NH:33][C:34]([NH:18][S:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:16])=[O:17])=[O:35])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 922592,6-Diisopropylphenyl isocyanateHCID 196118321-Tetradecylsulfonamide

Product 1

HCID 19611841N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)ureaYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-tetradecylsulfonamide (9.0 g, 32.4 mmoles) in DMF (90 mL) was added dropwise to a stirred suspension of NaH (1.63 g, 68 mmoles) in 30 mL of DMF. The solution was stirred 60 minutes, then 2,6-diisopropylphenyl isocyanate (7.0 mL, 33 mmoles) was added dropwise. The mixture was stirred overnight at room temperature, then quenched by dropwise addition of 1M HCl. The mixture was then partitioned between H2O and ethyl acetate (500 mL each). The aqueous layer was further extracted with ethyl acetate. The combined ethyl acetate extracts were diluted with hexane (100 mL) and then washed exhaustively with H2O. The organic extracts were dried, filtered, and concentrated to a solid residue, which was triturated with ether and the solid isolated by suction filtration and dried. Isolated 9.70 g of solid, m.p. 135°-137° C.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customquenched by dropwise addition of 1M HCl
  3. customThe mixture was then partitioned between H2O and ethyl acetate (500 mL each)
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. additionThe combined ethyl acetate extracts were diluted with hexane (100 mL)
  6. washwashed exhaustively with H2O
  7. customThe organic extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated to a solid residue, which
  10. customwas triturated with ether
  11. customthe solid isolated by suction filtration
  12. customdried

Sources & evidence

ORD record
ord-07acdedbce4c47c190886d4bf4b9b23f
Source dataset
uspto-grants-1993_10
Patent number
US05254589

Reaction notes

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