Hydrochloric Acid → 2-Methyl-2-phenyl-propionic acid, dimethylamide

HRID 411898

反応式

HRID 411898 の反応式
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].S(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:23][N:24](Cl)[CH3:25].Cl>C1(C)C=CC=CC=1.O.C(OC)(C)(C)C>[CH3:23][N:24]([CH3:25])[C:3](=[O:4])[C:2]([CH3:6])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:1]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 132222-Phenylisobutyric acidHCID 24386Thionyl Chloride2 回HCID 123122N-Chlorodimethylamine

生成物 1

HCID 540072552-Methyl-2-phenyl-propionic acid, dimethylamide収率 88%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

Dissolve 2-methyl-2-phenyl-propionic acid (15.08, 91.2 mmol) in toluene (80 mL) and add, by dropwise addition over 5 minutes, thionyl chloride (15 mL, 206 mmol). Stir at room temperature overnight, add additional thionyl chloride (3 mL, 41.1 mmol) and heat to reflux for 1 hour. Remove excess thionyl chloride by azeotropic distillation with toluene (40 mL). Add toluene (20 mL) to the reaction mixture along with a solution of potassium carbonate (28.0 g, 203 mmol) in water (40 mL). Add, by dropwise addition, a 40% aqueous solution of dimethylamino hydrochloride (20 mL, 0.18 mol) without cooling and stir for 2 hours. Add tert-butylmethyl ether (75 mL) following by slow addition of aqueous HCl (2N, 75 mL) with vigorous stirring. Separate the organic layer and wash with aqueous HCl (2N, 75 mL), saturated sodium hydrogen carbonate (25 mL) and brine (50 mL). Dry the organic layer over (Na2SO4), filter, evaporate the filtrate in vacuo and purify by crystallization to give 2-methyl-2-phenyl-propionic acid, dimethylamide (15.35 g, 88%) as a white solid; mp 57-59° C.

後処理

  1. additionadd, by dropwise addition over 5 minutes
  2. temperatureheat
  3. temperatureto reflux for 1 hour
  4. distillationRemove excess thionyl chloride by azeotropic distillation with toluene (40 mL)
  5. additionAdd, by dropwise addition
  6. stirringstir for 2 hours
  7. customSeparate the organic layer
  8. washwash with aqueous HCl (2N, 75 mL), saturated sodium hydrogen carbonate (25 mL) and brine (50 mL)
  9. dry with materialDry the organic layer over (Na2SO4)
  10. filtrationfilter
  11. customevaporate the filtrate in vacuo
  12. custompurify by crystallization

出典と根拠

ORDレコード
ord-1b076deea83c4d1387cf4b86ba6e43cf
出典データセット
uspto-grants-2003_05
特許番号
US06559312B2

関連ノート

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