Aniline → N-[[[4-(6-bromo-1,3-benzodioxan-2-yl)phenyl]amino]carbonyl]-2,6,-difluorobenzamide

HRID 1708176Notes

Reaction equation

HRID 1708176 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)[O:8][CH2:9][C:4]=2[CH:3]=1.[H][H].C(=O)([O-])[O-].[K+].[K+].NC1C=CC=CC=1.[F:36][C:37]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:38]=1[C:39]([N:41]=[C:42]=[O:43])=[O:40]>C1(C)C=CC=CC=1.[Pt]>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:42]([NH:41][C:39](=[O:40])[C:38]4[C:44]([F:48])=[CH:45][CH:46]=[CH:47][C:37]=4[F:36])=[O:43])=[CH:12][CH:11]=3)[O:8][CH2:9][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 27333692,6-Difluorobenzoyl isocyanateHCID 189611956-Bromo-2-(4-nitrophenyl)-1,3-benzodioxanHCID 178418361HCID 178418361, compound

Product 1

HCID 18961193N-[[[4-(6-bromo-1,3-benzodioxan-2-yl)phenyl]amino]carbonyl]-2,6,-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 6-bromo-2-(4-nitrophenyl)-1,3-benzodioxan (2.05 g) in toluene (150 ml) was hydrogenated at ≤60 psi hydrogen pressure in the presence of 5% platinum/charcoal (0.5 g) and anhydrous potassium carbonate (0.5 g) at ambient temperature. The reaction mixture was filtered and evaporated under reduced pressure, azeotropically removing the water formed in the reaction. The resulting crude aniline derivative was redissolved in dry toluene (25 ml) and treated with 2,6-difluorobenzoyl isocyanate (1.2 g), warming briefly to approx. 60° C. then allowing the stirred reaction mixture to cool overnight. Cooling to 0°-5° C. afforded a precipitate of impure product which was purified by crystallisation from ethanol (0.52 g, 17%), mp 194°-195° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customazeotropically removing the water
  4. customformed in the reaction
  5. customthe stirred reaction mixture
  6. temperatureto cool overnight
  7. temperatureCooling to 0°-5° C.
  8. customafforded a precipitate of impure product which
  9. customwas purified by crystallisation from ethanol (0.52 g, 17%), mp 194°-195° C.

Sources & evidence

ORD record
ord-c76d30b020a842a4b830bb5e106f322f
Source dataset
uspto-grants-1994_10
Patent number
US05356924

Reaction notes

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