Sodium hydride → 2-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene
Reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][C:5]=1[CH3:12].Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=1>>[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][C:14]2[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH:19]=2)=[CH:6][C:5]=1[CH3:12]Participants
Procedure
To a suspension of anhydrous N,N-dimethylformaide (30 ml) containing sodium hydride (0.35 g, 55% (w/w)) was added 4-amino-3,5-dimethylphenol (1.10 g) and the mixture was stirred at room temperature for 15 minutes. To the mixture was added in limited amounts t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (2.29 g) and the mixture was stirred at 120° C. for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:3 as the eluant to afford the desired compound (2.27 g, Rf=0.24: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=1:3 as the eluant).
Workup
- additionTo a suspension of anhydrous N,N-dimethylformaide (30 ml)
- stirringthe mixture was stirred at 120° C. for 1 hour
- concentrationThe reaction mixture was concentrated
- custompartitioned between ethyl acetate and water
- dry with materialThe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was chromatographed on a silica gel column
Sources & evidence
- ORD record
- ord-937b193a25f546d1955f1f2d601ab803
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562849B1
Reaction notes
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