Benzhydrylamine → HCID 86686566, compound

HRID 1528088Notes

Reaction equation

HRID 1528088 reaction equation
[F:1][C:2]1[C:9](F)=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[NH:4][CH3:5].[C:14]1([CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>C(O)CCC>[C:22]1([CH:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:21][C:9]2[CH:8]=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:3]([NH:4][CH3:5])[C:2]=2[F:1])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 152800922,3-Difluoro-N-methyl-6-nitroaniline

Product 1

HCID 86686566HCID 86686566, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2,3-difluoro-N-methyl-6-nitroaniline (2.66 g), 1,1-diphenylmethanamine (5.18 g), diisopropylethylamine (4.56 g) and butan-1-ol (26.6 mL) was heated at 200° C. for 2 hr using a microwave reactor. To the reaction mixture was added saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.47 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a85524c99dfa41308a8728c1ea444c05
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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