Benzocaine → HCID 58223053, compound

HRID 2042689Notes

Reaction equation

HRID 2042689 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4](Cl)[N:3]=1.[F:10][C:11]([F:15])([F:14])[CH2:12][OH:13].N1C(C)=CC(C)=CC=1C.[NH2:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C.[NH2:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=1>CC(C)=O.CN1C(=O)CCC1.O>[OH:54][C:51]1[CH:52]=[CH:53][C:48]([CH2:47][NH:46][C:2]2[N:7]=[C:6]([O:13][CH2:12][C:11]([F:15])([F:14])[F:10])[N:5]=[C:4]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=3)[N:3]=2)=[CH:49][CH:50]=1

Participants

10

Reactant 6

HCID 2337BenzocaineHCID 64092,2,2-TrifluoroethanolHCID 79532,4,6-TrimethylpyridineHCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 974724-Hydroxybenzylamine

Product 1

HCID 58223053HCID 58223053, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2,4,6-trichloro-1,3,5-triazine (10 g) in acetone (210 mL) was added a solution of 2,2,2-trifluoroethanol (5.97 g) and 2,4,6-collidine (7.88 mL) in acetone (210 mL) dropwise over 1 hour. The resulting mixture was stirred at room temperature for 16 hours. All the solvents were removed under vacuum to give a residue which was diluted with NMP (100 mL) and ethyl 4-aminobenzoate (9.85 g), iPr2NEt (28.4 mL) were added. After stirring at room temperature for 6 hours, 4-(aminomethyl)phenol (7.35 g) was added. The resulting mixture was stirred for 16 hours at room temperature. The mixture was diluted with 300 mL of water and extracted with EtOAc (2×500 mL). The organic layers were combined, washed with brine (300 mL), dried over MgSO4 and concentrated. The residue was purified by recrystallization in MeOH to give ethyl 4-(4-(4-hydroxybenzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (13.6 g).

Workup

  1. customAll the solvents were removed under vacuum
  2. customto give a residue which
  3. additionwere added
  4. stirringAfter stirring at room temperature for 6 hours
  5. stirringThe resulting mixture was stirred for 16 hours at room temperature
  6. extractionextracted with EtOAc (2×500 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by recrystallization in MeOH

Sources & evidence

ORD record
ord-c96eb66e4a654fb49adda410e97e4591
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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