P-Toluenesulfonamide → HCID 53642132, compound

HRID 1061450Notes

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:20]=[CH:19][C:18]([CH:21](Br)[CH3:22])=[C:17]([CH2:24]Br)[CH:16]=1>CN(C=O)C>[Br:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[CH:21]([CH3:22])[N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=1)(=[O:12])=[O:11])[CH2:24]2

Participants

Conditions

Temperature: 60 °C

Procedure

3.97 g of about 60% sodium hydride was suspended in 70 ml of DMF, and 50 ml of DMF solution of 8.49 g of p-toluene sulfonamide in was added thereto, and the resulting mixture was stirred at 60° C. for 1 hour, and 50 ml of DMF solution of 17.70 g of 1-bromo-4-(1-bromoethyl)-3-bromomethylbenzene (3-7) was dropped thereto, which was stirred at the same temperature for 2 hours. The reaction solution was poured into ice water and extracted with chloroform and the resulting organic layer was dried over anhydrous magnesium sulfate, and thereafter, the solvent was distilled off under reduced pressure and the resulting residue was purified by chromatopraphy (eluent; hexane:chloroform=1:1) to obtain 14.13 g of 5-bromo-1-methyl-2-(p-toluene sulfonyl)isoindoline (3-8).

Workup

stirringwhich was stirred at the same temperature for 2 hours
extractionextracted with chloroform
dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customthe resulting residue was purified by chromatopraphy (eluent; hexane:chloroform=1:1)

Sources & evidence

ORD record: ord-129874e8a3bc4634bb0184550b8ea088
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525066B2

Reaction notes

Loading…