N-Methylaniline → HCID 14390315, compound

HRID 621961Notes

Reaction equation

HRID 621961 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:29])([F:28])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:23]([CH2:24][C:25]([OH:27])=O)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)=[CH:11][CH:10]=1.[CH3:30][NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>O.CN(C)C=O>[CH3:30][N:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:25](=[O:27])[CH2:24][N:23]1[C:18]2[N:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:12]1[CH:13]=[CH:14][C:9]([C:8]([F:7])([F:29])[F:28])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15617192HCID 15617192, compound

Product 1

HCID 14390315HCID 14390315, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (1.91 g, 0.015 mole) was added dropwise (slowly) to a stirred and chilled (5°-10° C.) solution of 2-(4-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.5g, 0.014 mole) and anhydrous dimethylformamide (50 ml). The reaction mixture was heated at 55°-60° C. for 4 hours, cooled, and added dropwise to a stirred and chilled (5°-10° C.) solution of N-methylaniline (1.60 g, 0.015 mole), triethylamine (1.52 g, 0.015 mole), and anhydrous dimethylformamide (50 ml). The reaction mixture was stirred at room temperature overnight and then poured into water (300 ml). The mixture was extracted with methylene chloride (3×50 ml). The combined organic extracts were washed with potassium bicarbonate solution (2×30 ml), water (30 ml), dried over sodium sulfate and concentrated in vacuo. Recrystallization twice from isopropyl ether-petroleum ether gave 1.5 g (24 %) of off-white needles, mp 158°-159° C.

Workup

  1. temperatureThe reaction mixture was heated at 55°-60° C. for 4 hours
  2. temperaturecooled
  3. additionadded dropwise to
  4. stirringa stirred
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. extractionThe mixture was extracted with methylene chloride (3×50 ml)
  7. washThe combined organic extracts were washed with potassium bicarbonate solution (2×30 ml), water (30 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customRecrystallization twice from isopropyl ether-petroleum ether

Sources & evidence

ORD record
ord-e634f6151dbd4b4a8c336f05c3d14d9d
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

Loading…