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Hydrochloric Acid → N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide

HRID 526724
ノート
印刷プレビュー

反応式

HRID 526724 の反応式
[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:26])[CH2:24]Br)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=[O:29])C.[K+].Cl.C(Cl)Cl>C(O)(=O)C>[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:26])[CH2:24][OH:29])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 71502814N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide

生成物 1

HCID 71152063N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide収率 96.1%

試薬・触媒・溶媒 1

HCID 176
Acetic Acid
溶媒

反応条件

温度
112.5 °C

実験手順

A mixture of N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide (16 g, 36.3 mmol) and potassium acetate (8.90 g, 91 mmol) in acetic acid (130 ml) was heated to 110-115° C. (slow reflux visible) and stirred for 1 hour (complete by HPLC). Cooled, acetic acid (80 ml) removed under reduced pressure, the residue distributed between DCM (120 ml) and water (120 ml). The organic phase was washed with water, evaporated to half of the volume, diluted with 2-propanol (65.0 ml), the rest of DCM removed. Water (18.20 ml) was added followed by concentrated hydrochloric acid (2.102 ml, 25.4 mmol), residual DCM was distilled off at atmospheric pressure until head temperature reached 77° C., then stirred under reflux for 3 hours. Diluted with water (65 ml), 2-propanol removed at 60° C./180 mbar, to the biphasic residue EA (80 ml) was added followed by sodium bicarbonate with stirring until evolution of gas stopped. The organic phase was dried (MgSO4), evaporated to dryness to give N-benzyl-N-(4-hydroxy-3-oxobutyl)-2-nitrobenzenesulfonamide (13.2 g, 34.9 mmol, 96% yield).

後処理

  1. temperature(slow reflux visible)
  2. temperatureCooled
  3. customacetic acid (80 ml) removed under reduced pressure
  4. washThe organic phase was washed with water
  5. customevaporated to half of the volume
  6. additiondiluted with 2-propanol (65.0 ml)
  7. customthe rest of DCM removed
  8. additionWater (18.20 ml) was added
  9. distillationwas distilled off at atmospheric pressure until head temperature
  10. customreached 77° C.
  11. stirringstirred
  12. temperatureunder reflux for 3 hours
  13. additionDiluted with water (65 ml), 2-propanol
  14. customremoved at 60° C./180 mbar
  15. additionto the biphasic residue EA (80 ml) was added
  16. stirringwith stirring until evolution of gas
  17. dry with materialThe organic phase was dried (MgSO4)
  18. customevaporated to dryness

出典と根拠

ORDレコード
ord-98fe2f9365dc4a0fa3109194162d6e9f
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346751B2

反応ノート

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