M-Phenylenediamine → HCID 86640288, compound

HRID 1258541Notes

Reaction equation

HRID 1258541 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH3:9][C:10]1[CH:18]=[C:17]([C:19]([F:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])[CH:16]=[C:15]([CH3:29])[C:11]=1[C:12](Cl)=[O:13]>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[NH2:7][C:3]1[CH:2]=[C:1]([NH:8][C:12](=[O:13])[C:11]2[C:10]([CH3:9])=[CH:18][C:17]([C:19]([F:28])([C:20]([F:21])([F:22])[F:23])[C:24]([F:25])([F:26])[F:27])=[CH:16][C:15]=2[CH3:29])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 7935M-PhenylenediamineHCID 59253395HCID 59253395, compound

Product 1

HCID 86640288HCID 86640288, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzene-1,3-diamine (4.48 g, 41.4 mmol) in anhydrous tetrahydrofuran (3 ml) under an atmosphere of nitrogen was added 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzoyl chloride (4.40 g, 13.8 mmol) (Example I4) dissolved in anhydrous tetrahydrofuran (3 ml). The reaction mixture was stirred at 70° C. for 48 hours. Then the reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give N-(3-amino-phenyl)-2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzamide (3.4 mg, 61% yield). 1H-NMR (CDCl3, 400 MHz): 7.34 (t, 1H), 7.30 (s, 2H), 7.15 (t, 1H), 6.75 (d, 2H), 6.52 (d, 2H), 2.46 (s, 6H) ppm.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-757506abfe284d2e807f65eb642ea53a
Source dataset
uspto-grants-2013_06
Patent number
US08466180B2

Reaction notes

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