Triethylamine → 4-chloro-N-[4-(2,2-diethoxyethoxy)-3-methoxyphenyl]-2-nitrobenzamide

HRID 1181338

Reaktionsgleichung

Reaktionsgleichung von HRID 1181338
[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[CH2:20]([O:22][CH:23]([O:35][CH2:36][CH3:37])[CH2:24][O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=1[O:33][CH3:34])[CH3:21].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][CH2:24][CH:23]([O:35][CH2:36][CH3:37])[O:22][CH2:20][CH3:21])=[C:27]([O:33][CH3:34])[CH:28]=2)=[O:8])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 804754-Chloro-2-nitrobenzoic acidHCID 114367644-(2,2-Diethoxyethoxy)-3-methoxyaniline

Produkt 1

HCID 113165804-chloro-N-[4-(2,2-diethoxyethoxy)-3-methoxyphenyl]-2-nitrobenzamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-nitro-4-chlorobenzoic acid (5.09, 25.2 mmol) in DCM (100 mL) was added oxalyl chloride (16.8 mL, 34 mmol, 2M in DCM) and DMF (5 drops). The solution was stirred for 1 h and then concentrated by rotary evaporation. The resulting acid chloride was dissolved in DCM. To a solution of 4-(2,2-diethoxyethoxy)-3-methoxyaniline (5.36 g, 21 mmol), triethylamine (4.2 g) and DMAP (0.48 g) in DCM at 0° C. was added the acid chloride solution in 4 portions over 15 min. The reaction was stirred for 18 h and the ice was allowed to melt. The solvents were removed by rotary evaporation and the residue partitioned between water and ethyl acetate. The organic layer was washed with brine, dried and concentrated. The product was purified by by silica gel column chromatography affording the intermediate as a yellow solid (7.91 g, 86%). 1H NMR (DMSO-D6): δ 1.18 (6H, t, J=6.9 Hz), 3.57 (2H, q, J=12.1 Hz), 3.67 (2H, q, J=12.2 Hz), 3.75 (s, 3H), 3.91 (2H, d, J=5.1 Hz), 4.79 (1H, t, J=5.1 Hz), 7.00 (1H, m), 7.18 (1H, d), 7.34 (1H, s), 7.82 (1H, d), 7.95 (1H, d), 8.26 (1H, s), 10.57 (1H, d). LCMS m/z=461 (m+Na+).

Aufarbeitung

  1. concentrationconcentrated by rotary evaporation
  2. dissolutionThe resulting acid chloride was dissolved in DCM
  3. stirringThe reaction was stirred for 18 h
  4. customThe solvents were removed by rotary evaporation
  5. customthe residue partitioned between water and ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe product was purified by by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-726c8e356584415f80c72854b77112de
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285557B2

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