Benzamide → HCID 67754289, Verbindung

HRID 483753

Reaktionsgleichung

Reaktionsgleichung von HRID 483753
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=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:4](=[O:6])[C:3]2[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:7]=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 160976-Methyl-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 15020328(3S,4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol

Produkt 1

HCID 67754289HCID 67754289, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methyl-6-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 and chromatographed (1:1 hexanes/ethyl acetate) to afford 2.5 g (62%) of a white solid: m.p. 204°-206° C.; 1H NMR (CDCl3): δ 8.02 (d, 1H), 7.58 (d, 1H), 7.48 (t, 1H), 7.20 (s, 1H), 7.04 (d, 1H), 6.82 (d, 1 H), 6.06 (d, 1H), 3.80 (t, 1H), 3.70 (br s, 1H), 2.56 (s, 3H), 1.52 (s, 3H), 1.31 (s, 3H).

Aufarbeitung

  1. concentrationThe crude mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane (10 mL)
  3. customchromatographed (1:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d2add3c02dae4436b92cc53ece9babf4
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225566

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