Dimethylformamide → HCID 18184930, compound

HRID 1358578Notes

Reaction equation

HRID 1358578 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([CH3:15])[C:8]=1C.Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])[CH:19]=1.[CH3:36]N(C)C=O>>[C:32]([O:31][C:29]([N:27]([C:20]1[CH:19]=[C:18]([O:14][C:10]2[C:9]([CH3:15])=[CH:8][C:7]([O:6][CH2:5][O:4][CH3:3])=[C:12]([CH3:13])[C:11]=2[CH3:36])[CH:23]=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[CH3:28])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamateHCID 18184922HCID 18184922, compound

Product 1

HCID 18184930HCID 18184930, compound

Conditions

Temperature
120 °C

Procedure

Sodium hydride (6.11 g, 55% suspension in mineral oil) was added to a solution of 4-methoxymethoxy-2,3,5-trimethylphenol (27.5 g) in dimethylformamide (300 ml). After stirring the mixture for 1 hour 4chloro-2-(N-t-butoxycarbonyl-N-methylamino)nitrobenzene (40.1 g) was added in small portions to the mixture and stirred at 120° C. for 2 hours. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=5:1 as the eluant to afford the title compound (57.0 g, Rf=0.55: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=4:1 as the eluant).

Workup

  1. additionwas added in small portions to the mixture
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-e21a190abc2342678752e272899a7744
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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