Potassium Carbonate → 1H-Isoindole-1,3(2H)-dione, 2-(4-((3,4-dihydro-2H-1-benzothiopyran-8-yl)oxy)butyl)-

HRID 1491806Notes

Reaction equation

HRID 1491806 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.Br[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:18]1(=[O:27])[N:17]([CH2:16][CH2:15][CH2:14][CH2:13][O:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[S:1][CH2:2][CH2:3][CH2:4]3)[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 1216173,4-dihydro-2H-1-benzothiopyran-8-ol

Product 1

HCID 30739241H-Isoindole-1,3(2H)-dione, 2-(4-((3,4-dihydro-2H-1-benzothiopyran-8-yl)oxy)butyl)-Yield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under argon and with stirring, 500 mg (3.01 mmol) of 8-thiochromanol and 930 mg (3.31 mmol) of N-(4-bromobutyl) phthalimide are dissolved in 4 cm3 of dimethylformamide (DMF). 1.25 g (9.03 mmol) of K2CO3 are added. The mixture is heated at 60° C. for 6 hours. The DMF is evaporated off. The residue is taken up in H2O. The product is extracted with CH2Cl2 and dried over MgSO4. Purification over a silica column (eluant: CH2Cl2) yields 1.08 g of the title compound (white solid).

Workup

  1. customThe DMF is evaporated off
  2. extractionThe product is extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. customPurification over a silica column (eluant: CH2Cl2)

Sources & evidence

ORD record
ord-070e3b7e91fb4cb2b60ecb7d7442e23f
Source dataset
uspto-grants-1994_12
Patent number
US05371103

Reaction notes

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