N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamide → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-ethenylbenzenesulfonamide

HRID 1380469Notes

Reaction equation

HRID 1380469 reaction equation
C([Li])CCC.[Br-].C1([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)(=[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[CH:13]=[CH2:14])(=[O:42])=[O:43])=[O:39])[N:30]=1

Participants

5

Reactant 3

HCID 13097377N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamideHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 13772105N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-ethenylbenzenesulfonamide

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 3.7 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamide 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 washed with dilute 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 washed with dilute hydrochloric acid, water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-4074af18f0884eb8975337af4f039670
Source dataset
uspto-grants-1986_04
Patent number
US04582525

Reaction notes

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