Formaldehyde → HCID 59438395, compound

HRID 2177478Notes

Reaction equation

HRID 2177478 reaction equation
[CH3:1][NH2:2].[CH2:3]=O.CO[C:7](=[O:21])[CH2:8][CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[N+:11]([O-:13])=[O:12].[Na+].[Cl-]>O1CCOCC1.C(OCC)(=O)C>[Cl:20][C:16]1[CH:15]=[C:14]([C:10]2([N+:11]([O-:13])=[O:12])[CH2:1][N:2]([CH3:3])[C:7](=[O:21])[CH2:8][CH2:9]2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 6329MethylamineHCID 59438476HCID 59438476, compound

Product 1

HCID 59438395HCID 59438395, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred room temperature solution of 164 ul (1.940 mmol) methylamine (41% in water) in 1 ml dioxane was added 141 ul (1.940 mmol) formaldehyde (37% in water) dropwise (exothermic reaction). The mixture was stirred for 5 min and then a solution of 0.5 g (1.940 mmol) rac-4-(3-chloro-phenyl)-4-nitro-butyric acid methyl ester in 1.5 ml dioxane was added at once. The mixture was stirred at 65° C. for 6 h. The mixture was cooled to room temperature, ethyl acetate and a saturated NaCl solution were added. Aqueous phase was extracted 2 times with ethyl acetate. Combined organic phases were washed with a saturated NaCl solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 395 mg (76%) of the title compound as a colorless oil. MS (m/e): 269.2 (MH+).

Workup

  1. stirringThe mixture was stirred at 65° C. for 6 h
  2. extractionAqueous phase was extracted 2 times with ethyl acetate
  3. washCombined organic phases were washed with a saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-d2ba88a4b4cb46c19226e09e7a5fe4fa
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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