2,4,6-Trinitrotoluene → 4-Hydroxylamino-2,6-dinitrotoluene

HRID 17772

反応式

HRID 17772 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-])=[O:12])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.[OH-].[Na+]>C(OCC)(=O)C.Cl>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH:11][OH:12])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

参加物

6

反応物 3

HCID 83762,4,6-TrinitrotolueneHCID 10236NinhydrinHCID 14798Sodium Hydroxide

生成物 1

HCID 53754694-Hydroxylamino-2,6-dinitrotoluene収率 38.1%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of TNT (1.4 g, 6.16 mmol) in ethyl acetate (20 ml) was added a solution/suspension of stannous chloride (4.2 g, 22.22 mmol) in HCl (7.5 ml). An immediate yellow colour resulted. Stirring was continued until TLC (A) and ninhydrin development indicated the conversion of starting materials. The acidic solution was made basic by addition of NaOH solution (1M) and then extracted with saturated potassium chloride solution (4×10 ml). The organic layer was dried over sodiumsulphate and purified by column chromatography, eluting with dichloromethane to afford [7] as a yellow/orange solid (500 mg, 38%). Crystallisation from-chloroform afforded [7] as fine orange needles (220 mg). Rf (B) 0.18; δH(400 MHz; Acetone-d6) 2.29 (3H, s, CH3) 8.04 (1H, s, Ar—H) 8.19 (1H, s, Ar—H) 8.39 (1H, s, NOH) 8.42 (1H, s, NOH); m/z (EI−LR) 213 [(M) calc. for C7H7N3O5 213]; (Found C, 38.02; H, 2.07; N, 18.84. C7H7N3O5 requires C, 39.43; H, 3.28; N, 19.72%).

後処理

  1. customAn immediate yellow colour resulted
  2. extractionextracted with saturated potassium chloride solution (4×10 ml)
  3. dry with materialThe organic layer was dried over sodiumsulphate
  4. custompurified by column chromatography
  5. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-93c95c13ff9043a596b858197e3d206d
出典データセット
uspto-grants-2010_06
特許番号
US07741102B2

関連ノート

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