Tetrahydrofuran → HCID 19874945, compound

HRID 465632Notes

Reaction equation

HRID 465632 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)C2C=CC=CC=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[CH:23]([C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH2:28])([CH3:25])[CH3:24].CCN([CH2:41][CH3:42])CC.C1C[O:46][CH2:45]C1>>[CH3:34][CH:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:26]([CH:23]([CH3:25])[CH3:24])[C:27]=1[NH:28][C:45](=[O:46])[CH:17]([NH:10][S:7]([N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)(=[O:8])=[O:9])[CH2:22][C:21]1[CH:20]=[CH:19][CH:18]=[CH:42][CH:41]=1)[CH3:35]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 54251332HCID 54251332, compound

Product 1

HCID 19874945HCID 19874945, compoundYield 85%

Procedure

2.0 g (6.36 mmol) of the N-morpholinosulfonylphenylaniline was added to ice-cold SOCl2 (4 mL), and the reaction mixture was gradually warmed to room temperature and stirred overnight at room temperature. The solvent was evaporated under rotary evaporator. Toluene (10 mL) was added and the solution was evaporated. This process was repeated twice to remove any excess HCl(g). This was dissolved in THF (20 mL) and added slowly to a solution of 2,6-diisopropylaniline (1.0 g, 5.72 mmol) and Et3N (1.3 mL, 12.7 mmol) in THF (20 mL). The solution was stirred overnight at room temperature to complete the reaction. THF was evaporated, the residue was dissolved in CH2Cl2, and the solution was washed successively with 1N HCl, saturated NaHCO3, and brine. The solution was dried over anhydrous MgSO4, stripped and chromatographed (SiO2, 0-2% MeOH/CHCl3) to give 3 g (85%) of the desired product.

Workup

  1. customThe solvent was evaporated under rotary evaporator
  2. additionToluene (10 mL) was added
  3. customthe solution was evaporated
  4. customto remove any excess HCl(g)
  5. dissolutionThis was dissolved in THF (20 mL)
  6. stirringThe solution was stirred overnight at room temperature
  7. customthe reaction
  8. customTHF was evaporated
  9. dissolutionthe residue was dissolved in CH2Cl2
  10. washthe solution was washed successively with 1N HCl, saturated NaHCO3, and brine
  11. dry with materialThe solution was dried over anhydrous MgSO4
  12. customchromatographed (SiO2, 0-2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-e4e40bcbaab94dd099bafbea836ae177
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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