2-Acetyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-isopropenylbenzenesulfonamide

HRID 1164178Notes

Reaction equation

HRID 1164178 reaction equation
C([Li])CCC.[Br-].[C:7]1([C:13]([PH3+])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2C=CC=CC=2)C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[N:32]=[C:31]([NH:37][C:38]([NH:40][S:41](C2C=CC=CC=2C(=O)C)(=[O:43])=[O:42])=[O:39])[N:30]=1>O1CCCC1>[CH3:27][O:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[N:32]=[C:31]([NH:37][C:38]([NH:40][S:41]([C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:13]([CH3:7])=[CH2:14])(=[O:42])=[O:43])=[O:39])[N:30]=1

Participants

5

Reactant 3

HCID 130972992-Acetyl-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamideHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 13097390N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-isopropenylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 0.02 mol of n-butyllithium in 20 ml of anhydrous tetrahydrofuran is added 3.6 g of triphenylmethylphosphonium bromide. The above solution is stirred at room temperature for 4 hours. A slurry of 3.8 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-acetylbenzenesulfonamide in 30 ml of dry tetrahydrofuran is then added dropwise. The resulting mixture is refluxed overnight and allowed to cool to room temperature. The precipitate is removed by suction filtration and washed with methylene chloride. The combined filtrates are then washed with diluted hydrochloric acid, water, dried and evaporated to dryness to yield the desired product.

Workup

  1. temperatureThe resulting mixture is refluxed overnight
  2. temperatureto cool to room temperature
  3. customThe precipitate is removed by suction filtration
  4. washwashed with methylene chloride
  5. washThe combined filtrates are then washed with diluted hydrochloric acid, water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a0e5b5ed0df64f8c86a4690131ea77f9
Source dataset
uspto-grants-1983_01
Patent number
US04368069

Reaction notes

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