Hydrochloric Acid → HCID 68295566、化合物

HRID 572522ノート

反応式

HRID 572522 の反応式
[CH3:1][C:2]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[C:8]([N:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:11])=[O:9])=O.C[O-].[Na+].Cl.CC1C=CC(S(O)(=O)=O)=CC=1>CO.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:3]=1[C:4]1[C:6]2[C:7](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:8](=[O:9])[N:10]([CH3:11])[C:12]=1[C:13]([O:15][CH3:16])=[O:14]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acid2 回HCID 10942334Sodium MethoxideHCID 68295574HCID 68295574、化合物

生成物 1

HCID 68295566HCID 68295566、化合物収率 53%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

An ice cold mixture of methyl 2-(2-(2,4-dimethylbenzoyl)-N-methylbenzamido)acetate (60 g, 177 mmol) in methanol (400 mL) was treated with sodium methoxide (42.0 g, 194 mmol) and the resultant was allowed to stir at ambient temperature for 1 hour. The mixture was cooled to 0° C., treated with HCl (21.78 mL, 265 mmol) and then concentrated. The residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude intermediate was treated with Toluene (400 mL) and pTsOH (16.81 g, 88 mmol) and the mixture was heated at 120° C. for 1 hour. Additional pTsOH (16.81 g, 88 mmol) was added and the mixture was stirred at 120° C. overnight. LCMS indicated complete reaction. The mixture was concentrated and the residue was dissolved in ethyl acetate. The organic phase was washed with water, then brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-60% EA on hexane) to give the desired product as a white solid (24 g, 53%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.48-8.57 (m, 1 H) 7.50-7.58 (m, 2 H) 7.10-7.14 (m, 1 H) 7.04 (s, 3 H) 3.61 (s, 3 H) 3.54 (s, 3 H) 2.39 (s, 3 H) 2.04 (s, 3 H); LC/MS (m/z) ES+=322 (M+1).

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. temperaturethe mixture was heated at 120° C. for 1 hour
  9. stirringthe mixture was stirred at 120° C. overnight
  10. customreaction
  11. concentrationThe mixture was concentrated
  12. dissolutionthe residue was dissolved in ethyl acetate
  13. washThe organic phase was washed with water
  14. dry with materialbrine, dried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe residue was purified on silica gel (0-60% EA on hexane)

出典と根拠

ORDレコード
ord-cbc2c3b3df704f6b81f3f3bcbaee0164
出典データセット
uspto-grants-2015_05
特許番号
US09029391B2

反応ノート

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