Water → 2-[2-(p-toluenesulfonyloxy)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione

HRID 1941257Notes

Reaction equation

HRID 1941257 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[C:10]3[C:11]=2[C:6](=[C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]2=[CH:9]3)[C:5]1=[O:22].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>N1C=CC=CC=1>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:1][CH2:2][CH2:3][N:4]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][CH:17]=[C:10]4[C:11]=3[C:6](=[C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]3=[CH:9]4)[C:5]2=[O:22])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21460418HCID 21460418, compound

Product 1

HCID 214604202-[2-(p-toluenesulfonyloxy)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.01 g (3.5 mmol) of 2-(2-hydroxyethyl)-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione in 10 ml of pyridine is treated with 0.69 g (3.6 mmol) of p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 24 hours and poured into 50 ml of cold water. The solid is collected, washed with water, dried in vacuo, and crystallized from dimethylformamide water to give 1.2 g (77%) of 2-[2-(p-toluenesulfonyloxy)ethyl]-1,2-dihydro-3H-dibenz-[de,h]isoquinoline-1,3-dione. M.p. 240° C.

Workup

  1. customThe solid is collected
  2. washwashed with water
  3. customdried in vacuo
  4. customcrystallized from dimethylformamide water

Sources & evidence

ORD record
ord-b0e054fac6ef4454a2e85e555c858537
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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