Phenol → HCID 49869075, compound

HRID 450147Notes

Reaction equation

HRID 450147 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[C:11]1[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:14]=[C:13]([N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]=[C:24]2[CH:32]([F:34])[F:33])[N:12]=1.COCCOCCN(CCOCCOC)CCOCCOC>O.O1CCOCC1>[F:34][CH:32]([F:33])[C:24]1[N:23]([C:13]2[N:14]=[C:15]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[N:16]=[C:11]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:12]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 220368724-(4-chloro-6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine

Product 1

HCID 49869075HCID 49869075, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Phenol (200 mg, 21 mmol) and NaOH (85 mg, 21 mmol) were combined in water to give a clear solution, which was then evaporated to dryness. 1-[4-Chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (184 mg, 0.5 mmol) and tris[2-(2-methoxyethoxy)ethyl]amine (TDA-1; 16 mg, 0.05 mmol) were added and the mixture was heated under reflux in dioxane (10 mL) for 2 hr. After cooling, the mixture was diluted with water to give a white solid, which was collected and recrystallised from MeOH to give 93 mg (44% yield) of 2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-phenoxy-1,3,5-triazin-2-yl]-1H-benzimidazole: mp 228-231° C.; 1H NMR (CDCl3) δ 8.06 (d, J=8.2 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.49 (br t, J=7.9 Hz, 2H), 7.36 (br t, J=7.5 Hz, 2H), 7.30 (dt, J=7.6, 1.1 Hz, 1H), 7.22 (m, 2H), 7.11 (t, JHF=53.6 Hz, 1H), 3.99-3.93 (m, 4H), 3.86-3.79 (m, 4H); Anal. Calc. for C21H18F2N6O2: C, 59.4; H, 4.3; N, 19.8. Found: C, 59.65; H, 4.2; N, 19.9%.

Workup

  1. customto give a clear solution, which
  2. customwas then evaporated to dryness
  3. temperaturethe mixture was heated
  4. temperatureAfter cooling
  5. customto give a white solid, which
  6. customwas collected
  7. customrecrystallised from MeOH

Sources & evidence

ORD record
ord-ce718d33d4e24d9d8ba548f9604795f7
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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