Triethylamine → HCID 57193624, compound

HRID 417315Notes

Reaction equation

HRID 417315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.O=S(Cl)Cl.C(N(CC)CC)C.C[Si]([CH:30]=[N+:31]=[N-:32])(C)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCCCCC.O1CCCC1.CN(C=O)C>[N+:31](=[CH:30][C:6]([C:5]1[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:8])=[N-:32]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 787643-Methoxy-4-nitrobenzoic acidHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium Bicarbonate

Product 1

HCID 57193624HCID 57193624, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Step A To a solution of 3-methoxy-4-nitrobenzoic acid (Alfa) (10 g, 51 mmol) in toluene (75 mL) was added SOCl2 (11.5 g, 97 mmol), and a catalytic amount of DMF. The mixture was heated at refluxing for 3 h, then cooled to room temperature. The mixture was concentrated. The residue was dissolved into tetrahydrofuran (125 mL) and triethylamine (8.4 g, 83 mmol), and the temperature of the mixture was lowered to 0° C. A hexane solution (Alfa, 2 M) of (trimethylsilyl)diazomethane (41 mL, 83 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The mixture was poured into an aqueous saturated NaHCO3 solution, extracted with ethyl acetate three times. The combined organic extract was washed with brine, dried over MgSO4, and concentrated to give crude 2-diazo-1-(3-methoxy-4-nitro-phenyl)-ethanone as a brown oil (Yield 5 g, 45%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat refluxing for 3 h
  3. concentrationThe mixture was concentrated
  4. customwas lowered to 0° C
  5. extractionextracted with ethyl acetate three times
  6. extractionThe combined organic extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b8e47959b2ae43e09eaa3fc6b5105b81
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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