Benzenamine, 4-(1-methylpropyl)- → HCID 63110040, compound

HRID 1846266Notes

Reaction equation

HRID 1846266 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])OC(=O)[NH:7][C:6]=2[CH:13]=1.[CH:14]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([CH2:16][CH3:17])[CH3:15]>CN(C=O)C>[NH2:7][C:6]1[CH:13]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[C:10]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([CH:14]([CH2:16][CH3:17])[CH3:15])=[CH:19][CH:20]=1)=[O:11]

Participants

4

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 63110040HCID 63110040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
116 °C

Procedure

To a solution of 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (1.00 g, 5.52 mmol) in anhydrous DMF (15 mL), 4-(sec-butyl)-aniline (B) (0.824 g, 5.52 mmol) was added and the reaction mixture was heated at 116° C. for 16 hours. The product was extracted with ethyl acetate and washed with brine. The solvent was evaporated in vacuo to leave a crude material which was purified by column chromatography (silica gel; 230-400 mesh; ethyl acetate/hexane=1:9) to give 2-amino-N-(4-sec-butyl-phenyl)-4-fluoro-benzamide (N) as white solid. Yield: 0.92 g (58%).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washwashed with brine
  3. customThe solvent was evaporated in vacuo
  4. customto leave a crude material which
  5. customwas purified by column chromatography (silica gel; 230-400 mesh; ethyl acetate/hexane=1:9)

Sources & evidence

ORD record
ord-03809669217847438386e987ffec98a4
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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