2,2,2-Trifluoroethanol → HCID 25227404, compound

HRID 907412Notes

Reaction equation

HRID 907412 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Cl[C:10]1[CH:15]=[C:14](Cl)[N:13]=[C:12]([NH:17][C:18](=[O:30])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:11]=1>C1COCC1>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][C:10]1[CH:15]=[C:14]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[N:13]=[C:12]([NH:17][C:18](=[O:30])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:11]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 57651846HCID 57651846, compound

Product 1

HCID 25227404HCID 25227404, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (272 mg, 6.8 mmol, 60% in mineral oil) was added to a solution of 2,2,2-trifluoroethanol (1.5 g, 15 mmol) in anhydrous THF (15 mL) at 0° C. and the mixture stirred for 20 min. To this mixture was added N′-[4,6-dichloropyrimidin-2-yl]-N-[4-(trifluoromethyl)phenyl]urea (1.14 g, 3.24 mmol) and stirred at 0° C. for 1 h. The cooling bath was removed and the mixture allowed to warm to room temperature. The mixture was warmed to 45° C. and stirred for additional 18 h. The mixture was poured into water and stirred for 10 min and filtered to afford 1 (1.4 g, 68% yield): m.p. 167-168° C.; 1H NMR (DMSO-d6) δ 10.44 (bs, 1H), 10.28 (bs, 1H), 7.76 (d, J=6 Hz, 2H), 7.69 (d, J=6 Hz, 2H), 6.29 (s, 1H), 5.13 (q, J=9.0 Hz, 4H); ESI/MS 476.92 (M−H), 478.95 (M+H)

Workup

  1. stirringstirred at 0° C. for 1 h
  2. customThe cooling bath was removed
  3. temperatureThe mixture was warmed to 45° C.
  4. stirringstirred for additional 18 h
  5. additionThe mixture was poured into water
  6. stirringstirred for 10 min
  7. filtrationfiltered

Sources & evidence

ORD record
ord-35543d7121134f228036a19a291a54b1
Source dataset
uspto-grants-2011_09
Patent number
US08013154B2

Reaction notes

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