Triphenylphosphine → HCID 21842622、化合物

HRID 1737448ノート

反応式

HRID 1737448 の反応式
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]([CH2:42][CH2:43][CH2:44]O)[CH2:30][N:31]([CH3:41])[S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:26]=[CH:27][CH:28]=1>C(#N)C>[Br:1][CH2:44][CH2:43][CH2:42][CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[CH2:30][N:31]([CH3:41])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 21842614N-(2-(3-Chlorophenyl)-5-hydroxypentyl)-N-methylbenzenesulfonamide

生成物 1

HCID 21842622HCID 21842622、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Bromine was added to a solution of triphenylphosphine (41.4 mg, 0.158 mmol) in 0.50 mL of acetonitrile until the red color persisted, and a small additional quantity of triphenylphorsphine was then added to consume the excess bromine. A solution of N-(2-(3-chlorophenyl)-5-hydroxypentyl)-N-methylbenzenesulfonamide (38.7 mg, 0.105 mmol) in 0.3 mL of acetonitrile was added. After stirring for 1 h, the reaction was quenched by a solution of sodium sulfite (20 mg) dissolved in 1.0 mL of water. The mixture was diluted with 15 mL of sodium bicarbonate and extracted with 2×20 mL of ethyl acetate. The organic layers were washed with 15 mL of brine, dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography on silica gel, eluting with of 10% ethyl acetate in hexane to give 23 mg the title compound.

後処理

  1. additiona small additional quantity of triphenylphorsphine was then added
  2. customto consume the excess bromine
  3. customthe reaction was quenched by a solution of sodium sulfite (20 mg)
  4. dissolutiondissolved in 1.0 mL of water
  5. additionThe mixture was diluted with 15 mL of sodium bicarbonate
  6. extractionextracted with 2×20 mL of ethyl acetate
  7. washThe organic layers were washed with 15 mL of brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography on silica gel
  11. washeluting with of 10% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-240198b4a6924a729796830aac143154
出典データセット
uspto-grants-1999_10
特許番号
US05962462

反応ノート

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