Benzamide → N-[(3S,4R)-3-Hydroxy-2,2-dimethyl-6-(trifluoromethoxy)-chroman-4-yl]-5-methyl-2-nitrobenzamide
Reaction equation
[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]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- concentrationThe crude mixture was concentrated in vacuo
- additiondiluted with dichloromethane (10 mL)
Sources & evidence
- ORD record
- ord-62ec6949b17c4aada7d699614116470c
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05225566
Reaction notes
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