2-Chloro-5-nitrobenzenesulfonic acid → 2-Chloro-5-nitrobenzenesulfonamide

HRID 1038159

反応式

HRID 1038159 の反応式
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[S:15]([OH:18])(=O)=[O:16].S(Cl)(Cl)(=O)=O.[OH-].[NH4+:25]>C1(C)C=CC=CC=1.O1CCCC1.CN(C)C=O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[S:15]([NH2:25])(=[O:18])=[O:16]

参加物

8

反応物 4

HCID 73102-Chloro-5-nitrobenzenesulfonic acidHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 24648Sulfuryl chloride

生成物 1

HCID 667842-Chloro-5-nitrobenzenesulfonamide収率 42.4%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of thionyl chloride (11 mL) and 2-chloro-5-nitro-benzenesulfonic acid (4.78 g, 20.1 mmol) was added N,N-dimethylformamide (0.92 μL) and the reaction mixture was heated at reflux for 4 h. The reaction mixture was then carefully quenched by pouring it into water and the product was isolated by vacuum filtration. The sulfonyl chloride was dissolved in a minimal amount of toluene and then added to a mixture of concentrated aqueous ammonium hydroxide solution (25 mL) and tetrahydrofuran (25 mL) at −10° C. After stirring for 2 h the reaction was quenched by adding a 6.0 M aqueous hydrochloric acid solution until pH 4 was reached. The layers were separated and the organic layer was concentrated in vacuo to a slurry. Pentane was added and the product was isolated by vacuum filtration to afford 2-chloro-5-nitrobenzenesulfonamide (2.0 g, 8.48 mmol, 42.4%), as a solid. 1H NMR (400 MHz, DMSO-d6) δ: 7.94 (d, 1H, J=8.8 Hz), 7.97 (bs, 2H), 8.40 (dd, 1H, J1=8.6 Hz, J2=3.1 Hz), 8.64 (d, 1H, J=3.1 Hz).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe reaction mixture was then carefully quenched
  4. additionby pouring it into water
  5. customthe product was isolated by vacuum filtration
  6. customwas quenched
  7. additionby adding a 6.0 M aqueous hydrochloric acid solution until pH 4
  8. customThe layers were separated
  9. concentrationthe organic layer was concentrated in vacuo to a slurry
  10. additionPentane was added
  11. customthe product was isolated by vacuum filtration

出典と根拠

ORDレコード
ord-52ff3ac0473a4485aad946fec48cb56b
出典データセット
uspto-grants-2013_10
特許番号
US08546602B2

関連ノート

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