Isopropanol → HCID 86605516, compound

HRID 2374693Notes

Reaction equation

HRID 2374693 reaction equation
[CH:1]1([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:9]([CH3:18])[C:8]=2[S:19]([NH2:22])(=[O:21])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH2:25]([CH:27]1O[CH2:28]1)Cl.[CH3:30][CH:31](O)[CH3:32]>[Cl-].C([N+](CC)(CC)CC)C>[CH:27]1([C:11]2[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:9]([CH3:18])[C:8]([S:19]([NH2:22])(=[O:21])=[O:20])=[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:12]=2[CH3:13])[CH2:28][CH2:32][CH2:31][CH2:30][CH2:25]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 86605517HCID 86605517, compound

Product 1

HCID 86605516HCID 86605516, compound

Reagents, catalysts & solvents 1

HCID 5946Tetraethylammonium ChlorideCatalyst

Procedure

N,N*-cyclohexyl-2,5-dimethyl-1,3-benzenedisulfonamide (3.21 g, 0.0075 mol) was dissolved in 2-propanol (100 ml). 50% Sodium hydroxide (1.20 g) and tetraethyl ammonium chloride (0.05 g) were added to the solution and the solution refluxed for 1 hr. Epichlorohydrin (5 g) was added and the solution refluxed for 12.5 hrs and cooled to room temperature. The solvent, 2-propanol was removed in vacuo and the residue dissolved in dichloromethane and washed (2×) with water, dried over anhydrous MgSO4 and evaporated in vacuo. The crude bischlorohydrin was diluted with dichloromethane (50 ml) and added to a 50% sodium hydroxide (2.5 g) and tetraethyl ammonium chloride (50 mg) and the reaction mixture stirred for 2 hrs at room temperature. The organic layer was washed with water (2×), dried over anhydrous potassium carbonate and evaporated to give N,N*bis(2,3-epoxypropyl)-N,N*-bis(cyclohexyl)-2,5-dimethyl-1,3-benzenedisulfonamide. Recrystallization from hexane-ethyl acetate gave product mp 110-115° C. MS m/z 540 (M+ calcd for C26H40N2O6S2=540). H NMR (300 MHz, CDCl3) d 1.05-1.91 (m, 20, CH3), 2.45 (s, 3, CH3 aromatic), 2.52 (m, 2, epoxypropyl CH2), 2.77 (s, 3, CH3 aromatic), 2.81 (m, 2, CH2 epoxypropyl), 3.08 (m, 2, CH cyclohexyl), 3.14 (m, 2, CH, epoxypropyl), 3.57 (m, 4, CH2 epoxypropyl), 8.08 (s, 2, aromatic).

Workup

  1. temperaturethe solution refluxed for 1 hr
  2. temperaturethe solution refluxed for 12.5 hrs
  3. customThe solvent, 2-propanol was removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed (2×) with water
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated in vacuo
  8. additionThe crude bischlorohydrin was diluted with dichloromethane (50 ml)
  9. additionadded to a 50% sodium hydroxide (2.5 g) and tetraethyl ammonium chloride (50 mg)
  10. washThe organic layer was washed with water (2×)
  11. dry with materialdried over anhydrous potassium carbonate
  12. customevaporated

Sources & evidence

ORD record
ord-4c2b3926480e4cc6be5a7a0d1bbe2ed0
Source dataset
uspto-grants-2008_12
Patent number
US07462728B2

Reaction notes

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