Thionyl Chloride → tert-Butyl 4-((3,5-dimethoxy-4-methylbenzamido)methyl)-3-nitrobenzylcarbamate

HRID 1296773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296773
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:17][CH3:18])[C:15]=1[CH3:16])[C:10]([OH:12])=O.[NH2:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37]>CN(C=O)C.C1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[CH3:16])[C:10]([NH:19][CH2:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:23][C:22]=1[N+:36]([O-:38])=[O:37])=[O:12]

Komponenten

8

Edukt 3

HCID 24386Thionyl ChlorideHCID 37644863,5-Dimethoxy-4-methylbenzoic acidHCID 86595905tert-Butyl 4-(aminomethyl)-3-nitrobenzylcarbamate

Produkt 1

HCID 86595906tert-Butyl 4-((3,5-dimethoxy-4-methylbenzamido)methyl)-3-nitrobenzylcarbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

DMF (2 drops) and thionyl chloride (0.080 mL, 1.1 mmol) were sequentially added to a suspension of 3,5-dimethoxy-4-methyl benzoic acid (0.0995 g, 0.507 mmol) in benzene (2 mL). The reaction mixture was heated at reflux for 2 h, and then concentrated. The residue was dissolved in dichloromethane (1 mL) and then added dropwise to a solution of compound 65c (0.144 g, 0.512 mmol) and TEA (0.2 mL, 1.4 mmol) in dichloromethane (1 mL). The reaction mixture was stirred overnight at rt. The mixture was diluted with ethyl acetate and washed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution, dried, and concentrated to give compound 65d (0.233 g, 100%) as a yellow solid ESI-MS m/e 460.4 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane (1 mL)
  5. washwashed with 0.1 N HCl (2×) and saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8b8681b5c8754aa8a78b1315cb74837f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07247654B2

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