Water → HCID 178421809, compound

HRID 728351Notes

Reaction equation

HRID 728351 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[CH3:11].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.O.P(=O)(O)(O)O>CO>[OH-:12].[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:15]1[C:8]2[C:7]([O+:12]=[C:7]3[C:8]=1[CH:9]=[C:10]([CH3:11])[C:5]([NH:4][CH2:3][C:2]([F:13])([F:14])[F:1])=[CH:6]3)=[CH:6][C:5]([NH:4][CH2:3][C:2]([F:1])([F:14])[F:13])=[C:10]([CH3:11])[CH:9]=2)([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 6811Phthalic AnhydrideHCID 14876455HCID 14876455, compound2×

Product 1

HCID 178421809HCID 178421809, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Trifluoroethylamino-4-methylphenol (13.9 g; 0.068 mole) and phthalic anhydride (15.05 g; 0.102 mole-1.5 mole equivalents) were heated in a 500 ml round-bottomed, single-neck flask equipped with a short, water-cooled reflux condenser in a 160° oil bath for three hours. A temperature in the range of 150°-180° C. is acceptable. At the start of the reaction the melt was swirled from time to time to facilitate mixing. A further batch of 3-trifluoroethylamino-4-methylphenol (14.0 g; 0.068 mole) was warmed with 85% phosphoric acid (25 ml plus 10 ml) and was transferred to the cooled reaction mixture. The flask was heated for four hours at an oil bath temperature of 170°; again with occasional swirling. Methanol (170 ml; 25 ml per 0.01M) was added to the cooled but still warm reactants and the mixture was refluxed for twenty minutes. Crystals appeared almost immediately and the liquid was stored in a 4° refrigerator overnight. Filtration, washing with cold methanol, and drying gave 25.1 g of red-orange crystals. A second crop 0.9 g (total yield 73%) came from the filtrate kept several days at 4° C.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser in a 160° oil bath for three hours
  3. customin the range of 150°-180° C.
  4. customAt the start of the reaction the melt
  5. additionto facilitate mixing
  6. customwas transferred to the cooled reaction mixture
  7. temperatureThe flask was heated for four hours at an oil bath temperature of 170°
  8. temperaturecooled
  9. temperaturestill warm reactants and the mixture was refluxed for twenty minutes
  10. customwas stored in a 4°
  11. customrefrigerator overnight
  12. filtrationFiltration
  13. washwashing with cold methanol
  14. customdrying

Sources & evidence

ORD record
ord-138dddacb3be4dc59d300b4fb7f78f16
Source dataset
uspto-grants-1991_09
Patent number
US05047559

Reaction notes

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