Hydrochloric Acid → 4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2447

反応式

HRID 2447 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[NH:5][S:6]([C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)(=[O:8])=[O:7].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].Cl>C1COCC1.O>[OH:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([S:6]([NH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=2[O:2][CH3:1])(=[O:7])=[O:8])=[CH:17][CH:16]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 23335054-((2-Methoxyphenyl)sulfamoyl)benzoic acidHCID 4311764Sodium borohydride

生成物 1

HCID 196899084-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide収率 69.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In an atmosphere of argon and with cooling in an ice bath, 4-[(2-methoxyanilino)sulfonyl]benzoic acid (150 mg, 0.488 mmol) was dissolved in THF (5 ml), to which were subsequently added dropwise triethylamine (0.14 ml, 1.0 mmol) and ethyl chloroformate (50 μl, 0.509 mmol). After 30 minutes of stirring at the same temperature, the thus formed precipitate was removed by filtration, and the resulting filtrate was concentrated. The thus obtained residue was dissolved in 5 ml of THF, and, with cooling in an ice bath, sodium borohydride (46.5 mg, 1.22 mmol) and water (1 ml) were added to the resulting solution. After 40 minutes of stirring at the same temperature, the reaction mixture was adjusted to pH 4 to 5 with 2N hydrochloric acid and extracted with ether. The organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation, the resulting colorless oily material was purified by silica gel column chromatography (ether) to obtain 99.6 mg (69.6%) of the title compound in the form of colorless solid.

後処理

  1. temperatureIn an atmosphere of argon and with cooling in an ice bath
  2. customthe thus formed precipitate was removed by filtration
  3. concentrationthe resulting filtrate was concentrated
  4. dissolutionThe thus obtained residue was dissolved in 5 ml of THF
  5. temperaturewith cooling in an ice bath
  6. stirringAfter 40 minutes of stirring at the same temperature
  7. extractionextracted with ether
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried on anhydrous magnesium sulfate
  10. customAfter removing the solvent
  11. customby evaporation
  12. customthe resulting colorless oily material was purified by silica gel column chromatography (ether)

出典と根拠

ORDレコード
ord-5fabbe4482ff451aa260f688512ff2dd
出典データセット
uspto-grants-1998_03
特許番号
US05728835

関連ノート

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