Water → HCID 22634589, compound

HRID 1265284Notes

Reaction equation

HRID 1265284 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]=2[NH2:25])=[CH:5][CH:4]=1.[C:28](Cl)(=[O:32])[C:29](Cl)=[O:30].O>N1C=CC=CC=1>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=3)[C:10]=2[NH:25][C:28](=[O:32])[C:29]([NH:25][C:10]2[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=3)=[CH:12][CH:13]=[CH:14][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:26])[F:27])=[CH:4][CH:5]=2)=[O:30])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 22634587HCID 22634587, compound

Product 1

HCID 22634589HCID 22634589, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4,4″-Bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′-ylamine (700 mg, 1.84 mmol) in pyridine (5 mL) was treated with oxalyl chloride (73 μL, 0.837 mmol). The resulting suspension was stirred at rt overnight under Ar, then poured into H2O. The precipitate was filtered, washed with H2O and dried in vacuo. The resulting solid was crystallized from toluene/heptane, then recrystallized from toluene to afford N,N′-Bis-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′-yl)-oxalamide (430 mg).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customdried in vacuo
  4. customThe resulting solid was crystallized from toluene/heptane
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-6e416c4e0f8245a99671ddfe6a42ca74
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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