Dimethylformamide → HCID 21105760, compound

HRID 1354473Notes

Reaction equation

HRID 1354473 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C[N:26](C)C=O.C(Cl)(=O)C(Cl)=O>O1CCCC1>[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:26])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9818965HCID 9818965, compound

Product 1

HCID 21105760HCID 21105760, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 ml) of 4-[5-(4-trifluoromethylphenyl)-2-furyl]benzoic acid -(0.665 g) and N,N-dimethylformamide (0.1 ml) in tetrahydrofuran was added oxalyl chloride (0.209 ml) at 0° C. This mixture was stirred for 10 min., and concentrated. The residue was dissolved in acetonitrile (30 ml), and this solution was added dropwise to 25% aqueous ammonia (50 ml) at 0° C. The mixture was stirred for 10 min. and poured into water. The crystals were collected by filtration and recrystallized from ethanol to give 4-[5-(4-trifluoromethylphenyl)-2-furyl]benzamide (0.506 g, yield 76%) as a colorless crystalline powder. melting point: 263–264° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in acetonitrile (30 ml)
  3. additionthis solution was added dropwise to 25% aqueous ammonia (50 ml) at 0° C
  4. stirringThe mixture was stirred for 10 min.
  5. additionpoured into water
  6. filtrationThe crystals were collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5fe0efc9490a4712b34bd988f2695e73
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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