Methane → 2-(10-Bromodecyl)-1H-isoindole-1,3(2H)-dione

HRID 1788682Notes

Reaction equation

HRID 1788682 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[C:13]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[NH:14]1.[K].C>CN(C)C=O>[Br:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:14]1[C:15](=[O:22])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]1=[O:23]

Participants

6

Reactant 4

HCID 297MethaneHCID 6809PhthalimideHCID 2214831,10-DibromodecaneHCID 5462222Potassium

Product 1

HCID 5948562-(10-Bromodecyl)-1H-isoindole-1,3(2H)-dioneYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100.0 g of 1,10-dibromodecane and 50.0 g of 1H-isoindole-1,3(2H)-dione, potassium salt in 500 ml of N,N-dimethylformamide was stirred and heated on a steam bath for eight hours. The reaction mixture was clarified while hot with activated charcoal, then filtered. The material on the filter was washed with 100 ml of N,N-dimethylformamide. The filtrate and wash were combined and taken to dryness in vacuo. The residue was triturated with 100 ml of hexane. The insoluble product was collected, washed with 50 ml of hexane, then air dried and gave 81.0 g of 2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione.

Workup

  1. temperatureheated on a steam bath for eight hours
  2. filtrationfiltered
  3. washThe material on the filter was washed with 100 ml of N,N-dimethylformamide
  4. washThe filtrate and wash
  5. customThe residue was triturated with 100 ml of hexane
  6. customThe insoluble product was collected
  7. washwashed with 50 ml of hexane
  8. customair dried

Sources & evidence

ORD record
ord-40833ac0fa4e4b34abda5babec381081
Source dataset
uspto-grants-1987_08
Patent number
US04684654

Reaction notes

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