Sodium Hydroxide → 2-Chloro-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro-1(2H)-pyrimidinyl]benzoic acid

HRID 1645741Notes

Reaction equation

HRID 1645741 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]2=[O:25])=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[NH:16][C:15]2=[O:25])=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53635610HCID 53635610, compound

Product 1

HCID 198021202-Chloro-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro-1(2H)-pyrimidinyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 58.9 grams (0.156 mole) of isopropyl 2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H) pyrimidinyl]benzoate and 11.2 grams (0.28 mole) of sodium hydroxide in 1200 ml. of 50% ethanol was heated at 65° C. for 30 minutes and stirred for 2 hours. Evaporation under a reduced pressure removed the solvent. The residue was treated with 2.3 ml. of concentrated hydrochloric acid in 130 ml. of water. Filtration collected 45 grams of crude solid. The solid product was further dissolved in a solution of 10 grams (0.25 (mole) of sodium hydroxide in 600 ml. of water. The solution was cooled with an ice-water bath and then acidified to pH 2 with concentrated hydrochloric acid. The colorless precipitate was collected by filtration, rinsed with water and air-dried. The sample of 2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1 (2H) pyrimidinyl]benzoic acid weighed 40.7 grams (78%); m.p. 311°-2° C. 'H NMR (300 MHzm/DMSO-d6) δ 3.36 (broad,1H); 6.37 (S,1H); 7.45 (dd, J=9.3, 2.1 Hz,1H); 7.67 (d,J=9.3 Hz,1H); 7.79 (d, J=2.1 Hz, 1H), 12.48 (broad, 1H).

Workup

  1. customEvaporation under a reduced pressure
  2. customremoved the solvent
  3. additionThe residue was treated with 2.3 ml
  4. filtrationFiltration
  5. customcollected 45 grams of crude solid
  6. dissolutionThe solid product was further dissolved in a solution of 10 grams (0.25 (mole) of sodium hydroxide in 600 ml
  7. temperatureThe solution was cooled with an ice-water bath
  8. filtrationThe colorless precipitate was collected by filtration
  9. washrinsed with water
  10. customair-dried

Sources & evidence

ORD record
ord-948d6f0e7e69419bbc6fce3568754a0a
Source dataset
uspto-grants-1993_01
Patent number
US05176735

Reaction notes

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