Diethyl Ether → HCID 19775941, compound

HRID 1612573Notes

Reaction equation

HRID 1612573 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([N+:22]([O-])=O)[CH:14]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C(N(CC)CC)C.[CH3:32][CH:33](N)[CH2:34][OH:35].C(OCC)C>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([NH:22][CH:33]([CH3:32])[CH2:34][OH:35])[CH:14]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 51262-AminopropanolHCID 8471TriethylamineHCID 19775926HCID 19775926, compound

Product 1

HCID 19775941HCID 19775941, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The dinitrobenzene obtained in Step A (10.0 g, 27.3 mmol) was dissolved in dimethylformamide (40 cm3). Triethylamine (4.6 cm3, 32.7 mmol) and DL 2-aminopropanol (2.6 cm3, 32.7 mmol) were added, and the mixture stirred at room temperature for 17 hours, then at 50° C. for 4 hours. The mixture was cooled to room temperature, poured into diethyl ether (200 cm3) and washed with water (3×200 cm3). The ether layer was collected, dried (MgSO4), filtered and the solvent removed under reduced pressure to give a waxy yellow solid. Recrystallisation (ethyl acetate/hexane) gave DL-2-[5-(4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol -3-yloxy)-2-nitrophenylamino]-propane-1-ol (8.71 g) as an orange solid. m.p. 118°-120° C.

Workup

  1. waitat 50° C. for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water (3×200 cm3)
  4. customThe ether layer was collected
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto give a waxy yellow solid
  9. customRecrystallisation (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e2cfbf8329824bd58e72ea05e7b28c55
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

Loading…