Ethyl Acetate → HCID 89649707, compound

HRID 1479022Notes

Reaction equation

HRID 1479022 reaction equation
Cl.[F:2][C:3]([F:12])([F:11])[CH:4]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][NH:5]1.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+].F[C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=[O:33].CC(=O)OCC>CS(C)=O.O>[F:12][C:3]([F:2])([F:11])[CH:4]1[CH2:10][CH2:9][N:8]([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[CH:32]=[O:33])[CH2:7][CH2:6][NH:5]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 67970o-FluorobenzaldehydeHCID 151402Sodium Carbonate DecahydrateHCID 89650243HCID 89650243, compound

Product 1

HCID 89649707HCID 89649707, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-trifluoromethyl-[1,4]diazepane hydrochloride (1.17 g; 4.83 mmol; 1.2 eq.), sodium carbonate decahydrate (2.13 g; 20.14 mmol; 5 eq.) and 2-fluoro-benzaldehyde (500 mg; 4.03 mmol; 1 eq.) in DMSO (20 mL) and water (20 mL) was stirred at 160° C. for 4 hours. The solution was diluted EA and the organic layer washed with water (3×) then brine (2×), dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (15% to 33% EA in heptanes) afforded the title compound (350 mg, 32%) as a yellow oil. HPLC (max plot) 97.9%; Rt 5.23 min.

Workup

  1. washthe organic layer washed with water (3×)
  2. dry with materialbrine (2×), dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (15% to 33% EA in heptanes)

Sources & evidence

ORD record
ord-e3b1ab2f09094448a537929019043c27
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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