Diethyl Ether → HCID 19775943, compound

HRID 1612576Notes

Reaction equation

HRID 1612576 reaction equation
[Br: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>[Br: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 19775929HCID 19775929, compound

Product 1

HCID 19775943HCID 19775943, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The dinitrobenzene obtained in Step A (10.0 g, 24.3 mmol) was dissolved in N,N-dimethylformamide (60 cm 3). Triethylamine (5.1 cm3, 36.5 mmol) and DL 2-aminopropanol 2.9 cm3, 36.5 mmol) were added, and the mixture was stirred at room temperature for 21 hours, and then heated at 70° C. for a further 3 hours. The mixture was cooled to room temperature, poured into diethyl ether (500 cm3) and washed with water (3×300 cm3). The organic layer was dried (MgSO4), filtered and evaporated under reduced pressure to give DL 2-[5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol -3-yloxy)-2-nitrophenylamino]propan-1-ol (10.15 g) as an orange solid m.p 116°-118° C.

Workup

  1. temperatureheated at 70° C. for a further 3 hours
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water (3×300 cm3)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fcd9252c8177417794a546e36dcbcb52
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

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