Ethyl Acetate → HCID 22137850, compound

HRID 858321Notes

Reaction equation

HRID 858321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([O:22]COC)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].C(OCC)(=O)C>Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[C:14]([OH:22])[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:26]([F:27])([F:28])[F:29]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 22137857HCID 22137857, compound

Product 1

HCID 22137850HCID 22137850, compound

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

1-(4-Chloro-3-trifluoromethyl-phenyl)-3-(3-methoxymethoxy-5-trifluoromethyl-phenyl)-urea (100 mg, 0.25 mmol) from above was dissolved in a 1:1 solution of 3N HCl/ethyl acetate (20 mL) and stirred vigorously at room temperature for 16 h. Additional ethyl acetate was then added (50 mL) and the mixture was washed with water (2×50 mL), brine (50 mL), dried over Na2SO4, and concentrated. The resulting residue was purified using silica gel flash chromatography eluting with a 3:1 hexane/ethyl acetate solution. Similar fractions were pooled and concentrated to the title compound (72 mg, 72%) as an off-white solid. 1H NMR (CD3OD) δ 7.97 (d, J=2 Hz, 1 H), 7.64 (dd, J=2 Hz, J=8 Hz, 1H), 7.50 (d, J=8 Hz, 1H), 7.22 (s, 1H), 7.21 (s, 1H), 6.75 (s, 1H); Electrospray MS (MH+) m/z 399.

Workup

  1. washthe mixture was washed with water (2×50 mL), brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified
  5. washeluting with a 3:1 hexane/ethyl acetate solution
  6. concentrationconcentrated to the title compound (72 mg, 72%) as an off-white solid

Sources & evidence

ORD record
ord-5aa67c6710494000ba39639fdd18a9fb
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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