Benzamide → N-[(3S,4R)-3-Hydroxy-2,2-dimethyl-6-(trifluoromethoxy)-chroman-4-yl]-5-methyl-2-nitrobenzamide

HRID 483755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483755
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.S(Cl)(Cl)=O.[NH2:18][C@@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:29][C:30]([F:33])([F:32])[F:31])[CH:27]=2)[O:22][C:21]([CH3:35])([CH3:34])[C@H:20]1[OH:36].C(N(CC)CC)C.C(N)(=O)C1C=CC=CC=1>C1C=CC=CC=1.ClCCl>[OH:36][C@H:20]1[C@H:19]([NH:18][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:29][C:30]([F:33])([F:31])[F:32])[CH:27]=2)[O:22][C:21]1([CH3:35])[CH3:34]

Komponenten

8

Edukt 5

HCID 2331BenzamideHCID 8471TriethylamineHCID 183715-Methyl-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 15020328(3S,4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol

Produkt 1

HCID 67753930N-[(3S,4R)-3-Hydroxy-2,2-dimethyl-6-(trifluoromethoxy)-chroman-4-yl]-5-methyl-2-nitrobenzamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Methyl-2-nitrobenzoic acid (1.81 g, 10 mmol) was converted to the corresponding acid chloride by refluxing in benzene (30 mL) with thionyl chloride (1.66 g, 14 mmol) for 0.5 hours. The crude mixture was concentrated in vacuo and diluted with dichloromethane (10 mL). This solution was added to a cooled solution of (3S, 4R)-4-amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol (2.75 g, 10 mmol), triethylamine (1.39 mL, 10 mmol) and dichloromethane (25 mL). The crude benzamide was worked-up in a method similar to that in Example 1 to afford 3.37 g (82%) of a white solid: m.p. 185°-187° C., 1H NMR (DMSO-d6): δ 9.12 (d, 1H), 7.96 (d, 1H), 7.60 (s, 1H), 7.51 (d, 1H, 7.38 (s, 1H), 7.16 (d, 1H), 6.86 (d, 1H), 5.84 (d, 1H), 5.00 (t, 1H), 3.66 (m, 1H), 2.45 (s, 3H), 1.43 (s, 3H), 1.20 (s, 3H).

Aufarbeitung

  1. concentrationThe crude mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-62ec6949b17c4aada7d699614116470c
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225566

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