Sodium hydride → HCID 67528005, compound

HRID 1512175Notes

Reaction equation

HRID 1512175 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=2)=[C:6]([C:18]([F:21])([F:20])[F:19])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:24]1([CH:30]=[CH:31][C:32](Cl)=[O:33])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[Cl-].[NH4+]>CN(C=O)C>[CH:24]1([CH:30]=[CH:31][C:32]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]3[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=3[C:18]([F:19])([F:20])[F:21])=[CH:9][C:10]=2[N+:15]([O-:17])=[O:16])=[O:33])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 50994194HCID 50994194, compoundHCID 566232073-Cyclohexylprop-2-enoyl chloride

Product 1

HCID 67528005HCID 67528005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6′-fluoro-3-nitro-2′-trifluoromethyl-biphenyl-4-yl-amine (150 mg, 0.500 mmol, prepared as in STEP A above) in DMF (10 mL) was added 60% NaH (120 mg, 3 mmol) portion wise. The resulting mixture was stirred at room temperature for 15 min. and treated with 3-cyclohexyl-acryloyl chloride (172 mg, 1.00 mmol) in DMF (2 mL). The resulting mixture was stirred overnight and poured into saturated aqueous ammonium chloride solution (10 mL). The aqueous layer was extracted thrice with EtOAc (10 mL). The EtOAc layers were combined, dried over Na2SO4 and concentrated. The residue was purified on silica (EtOAc/hexane, 0:100 to 100:0, v/v) to yield 3-cyclohexyl-N-(6′-fluoro-3-nitro-2′-trifluoromethyl-biphenyl-4-yl)-acrylamide.

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. extractionThe aqueous layer was extracted thrice with EtOAc (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica (EtOAc/hexane, 0:100 to 100:0

Sources & evidence

ORD record
ord-3dc634287f5644999e8cdf642c0323c2
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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