Sulfuric Acid → HCID 21962913, compound

HRID 2211965Notes

Reaction equation

HRID 2211965 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][NH:6][C:7]([CH3:11])([CH3:10])[CH2:8][OH:9].O1[CH2:18][CH:17]1[CH2:19][N:20]1C(=O)C2C(=CC=CC=2)C1=O.S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][N:6]1[C:7]([CH3:11])([CH3:10])[CH2:8][O:9][CH:17]([CH2:19][NH2:20])[CH2:18]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 993601-Propanol, 2-(3,4-dichlorobenzylamino)-2-methyl-

Product 1

HCID 21962913HCID 21962913, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Intermediate 2 (0.260 g) and 2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.205 g) was heated at 80° C. under nitrogen for 3 h. The mixture was treated with concentrated sulphuric acid (0.3 ml) then stirred at 150° C. for 18 h. The mixture was treated with water (25 ml) then washed with ethyl acetate (2×25 ml). The dark aqueous phase was basified to ˜pH 11 using 5M aqueous sodium hydroxide then extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated under vacuum to give the title compound as a brown oil (0.225 g).

Workup

  1. washthen washed with ethyl acetate (2×25 ml)
  2. extractionthen extracted with ethyl acetate (2×25 ml)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b5371d9e4a044234946eaf27cdd0b86e
Source dataset
uspto-grants-2006_09
Patent number
US07101882B2

Reaction notes

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