Hydrochloric Acid → HCID 19862064, compound

HRID 1165534Notes

Reaction equation

HRID 1165534 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.F[C:10]1[CH:33]=[CH:32][C:13]([C:14]([C:16]2[CH:31]=[CH:30][C:19]([O:20][C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=3)[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:32]1[CH:33]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14]([C:16]1[CH:31]=[CH:30][C:19]([O:20][C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=1)=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 198620633-[4-(4-Fluorobenzoyl)phenoxy]benzoic acid

Product 1

HCID 19862064HCID 19862064, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of m-aminophenol (0.64 g, 5.87 mmol), 3-[4-(4-fluorobenzoyl)phenoxy]benzoic acid (2.0 g, 5.95 mmol), and anhydrous potassium carbonate (4.0 g) was stirred in dry dimethylsulfoxide (20 ml) at 120° C. under nitrogen for 48 hours. The cooled reaction mixture was poured into water and carefully neutralized with conc. hydrochloric acid to precipitate 2.58 g of a white solid. The crude product was digested in hot toluene, and the toluene solution (after decanting from a large quantity of gum) was allowed to stand overnight at 0° C. The crystals thus obtained were recrystallized to give 0.35 g of product, m.p. 144°-150° C. dec. (14%).

Workup

  1. customThe cooled reaction mixture
  2. customto precipitate 2.58 g of a white solid
  3. customthe toluene solution (after decanting from a large quantity of gum)
  4. customThe crystals thus obtained
  5. customwere recrystallized

Sources & evidence

ORD record
ord-2e1f89e83fba468e98a728c0b67a2fd5
Source dataset
uspto-grants-1990_03
Patent number
US04910282

Reaction notes

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