P-Toluenesulfonamide → HCID 18629321, compound

HRID 1061459Notes

Reaction equation

HRID 1061459 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1.[Br:14][C:15]1[CH:16]=[C:17]([F:25])[C:18]([CH2:23]Br)=[C:19]([CH2:21]Br)[CH:20]=1>CN(C=O)C>[Br:14][C:15]1[CH:20]=[C:19]2[C:18]([CH2:23][N:13]([S:10]([C:7]3[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=3)(=[O:12])=[O:11])[CH2:21]2)=[C:17]([F:25])[CH:16]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 18629356HCID 18629356, compound

Product 1

HCID 18629321HCID 18629321, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

1.17 g of about 60% sodium hydride was suspended in 30 ml of DMF, to which was added 15 ml of DMF solution of 2.50 g of p-toluene sulfonamide, and the resulting mixture was stirred at 60° C. for 1 hour. 15 ml of DMF solution of 5.02 g of 5-bromo-1,2-bis(bromomethyl)-3-fluorobenzene (3-13) was dropped thereto and the resulting mixture was stirred at the same temperature for 1 hour. The reaction solution was poured into ice water and the precipitated crystal was separated by filtering to obtain 5.10 g of 6-bromo-4-fluoro-2-(p-toluensulfonyl)isoindoline (3-14).

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  2. customthe precipitated crystal was separated
  3. filtrationby filtering

Sources & evidence

ORD record
ord-43ff1ab7320e4e84936436e6e2d69a61
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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