Water → N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 1528184ノート

反応式

HRID 1528184 の反応式
S(=O)(=O)(O)O.O.[CH3:7][N:8]([CH3:26])[S:9]([C:12]1[C:20]2[O:19]C(C(C)(C)C)=[N:17][C:16]=2[CH:15]=[CH:14][C:13]=1[Cl:25])(=[O:11])=[O:10]>O1CCOCC1>[NH2:17][C:16]1[C:20]([OH:19])=[C:12]([S:9]([N:8]([CH3:7])[CH3:26])(=[O:10])=[O:11])[C:13]([Cl:25])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 671285552-Tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide

生成物 1

HCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide収率 72%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

3.4 ml of sulfuric acid (63.59 mmol; 1.16 V) and 3.4 ml of water were added to a solution of 2.93 g of 2-tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide (9.25 mmol; 1.0 eq) in 13 ml of 1,4-dioxane. The reaction medium was refluxed for four and a half hours. The reaction medium was concentrated. 130 ml of 1 M sodium hydroxide were added to the residue (pH=10), followed by 400 ml of water. The solution was extracted with ethyl acetate (2×250 ml). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (250 g prepacked column: eluent heptane/ethyl acetate, from 20% to 40% of ethyl acetate, flow rate 100 ml/min). 1.66 g of 3-amino-6-chloro-2-hydroxy-N,N-dimethylbenzenesulfonamide were obtained. Yield=72%.

後処理

  1. temperatureThe reaction medium was refluxed for four and a half hours
  2. concentrationThe reaction medium was concentrated
  3. addition130 ml of 1 M sodium hydroxide were added to the residue (pH=10)
  4. extractionThe solution was extracted with ethyl acetate (2×250 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel (250 g prepacked column: eluent heptane/ethyl acetate, from 20% to 40% of ethyl acetate, flow rate 100 ml/min)

出典と根拠

ORDレコード
ord-919748f601604d0e8bb74afe563a7213
出典データセット
uspto-grants-2015_07
特許番号
US09090596B2

反応ノート

読み込み中…