Toluene → HCID 117770477, compound

HRID 1526359Notes

Reaction equation

HRID 1526359 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])(=O)C.[Na+].C1(C)C=CC=CC=1.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:2]=1[NH:1][C:26](=[O:27])[CH2:25][C:24](=[O:28])[CH3:23])#[N:5]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 12661Diketene2×HCID 517045Sodium AcetateHCID 27833922-Amino-3-fluorobenzonitrile

Product 1

HCID 117770477HCID 117770477, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) over 10 min at 0° C. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether/ethanol

Sources & evidence

ORD record
ord-9c0dc63ca8e4427d87e4d2fe5ed4a4b3
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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