N-methyl-2-pyrrolidone → 4-{[4-(4-Bromophenyl)pyrimidin-2-yl]amino}benzenesulfonamide

HRID 1715693Notes

Reaction equation

HRID 1715693 reaction equation
CN([CH:4]=[CH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=O)C.[NH:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:16]([NH2:18])=[NH:17].CN1C(=O)CCC1>O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:18]=[C:16]([NH:15][C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:26])=[O:27])=[CH:21][CH:20]=3)[N:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 6172441-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-oneHCID 178512579HCID 178512579, compound

Product 1

HCID 574467974-{[4-(4-Bromophenyl)pyrimidin-2-yl]amino}benzenesulfonamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A flask is charged with the 1-(4-bromo-phenyl)-3-dimethylamino-propenone (1.05 g, 4.10 mmol), 4-guanidino-benzenesulfonamide (1.33 g, 6.20 mmol), and NMP (30 ml). The reaction mixture is stirred at 120° C. for 20 h. The reaction mixture is cooled to room temperature, diluted with water, and filtered. The solid residue is washed with water and dried to yield 1.66 g of a white solid. MS (ESI) m/z 405.1; HRMS: calcd for C16H13BrN4O2S+H+, 405.00153; found (ESI-FTMS, [M+H]1+), 405.00158.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. washThe solid residue is washed with water
  4. customdried

Sources & evidence

ORD record
ord-d4748d8351f64745925345778e099815
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

Loading…