Benzenamine, 4-(1-methylpropyl)- → HCID 43702109, compound

HRID 1846283Notes

Reaction equation

HRID 1846283 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6]C(=O)O[C:9](=[O:10])[C:4]=2[CH:3]=1.[CH:14]([C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)([CH2:16][CH3:17])[CH3:15]>CN(C=O)C>[NH2:6][C:5]1[CH:12]=[CH:13][C:2]([F:1])=[CH:3][C:4]=1[C:9]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([CH:14]([CH2:16][CH3:17])[CH3:15])=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 2885605-Fluoroisatoic anhydride

Product 1

HCID 43702109HCID 43702109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (1.06 g, 5.90 mmol) in DMF (5 mL) was added 4-sec-butylphenylamine (1.95 mL, 11.8 mmol) at room temperature. The suspension was heated at 70° C. for 2 days, and cooled to room temperature. The reaction mixture was poured into crushed ice (150 mL), and extracted with dichloromethane. The organic layer was dried over Na2SO4, and evaporated under vacuum. The residue was purified by flash column chromatography on a Biotage (40 M silica column), using a gradient of hexane:ethyl acetate (9:1 to 8:2) mixture as eluent to afford 2-amino-N-(4-sec-butylphenyl)-5-fluorobenzamide. Yield: 1.16 g (69%).

Workup

  1. temperaturecooled to room temperature
  2. additionThe reaction mixture was poured
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated under vacuum
  6. customThe residue was purified by flash column chromatography on a Biotage (40 M silica column)

Sources & evidence

ORD record
ord-1355f2ca03334437955617ee5acdc695
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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