Sodium Carbonate → HCID 68579808, compound

HRID 2244583Notes

Reaction equation

HRID 2244583 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]([CH3:14])[CH3:13])[C:6]([NH2:8])=O.O=P(Cl)(Cl)Cl.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]([CH3:13])[CH3:14])[C:6]#[N:8]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 59644853HCID 59644853, compound

Product 1

HCID 68579808HCID 68579808, compoundYield 90.8%

Conditions

Temperature
105 °C

Procedure

A mixture of the above benzamide (0.220 g, 1.25 mmol), POCl3 (1 mL) and diisopropylethylamine (0.5 mL) was heated to 105° C. for 16 hours and then cooled to room temperature. The solution was poured into ice water and neutralized with sodium carbonate, then extracted with EtOAc (2×20 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography eluting with hexanes/EtOAc (2:1) afforded 3-methoxy-4-dimethylaminobenzonitrile as an oil (0.20 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography
  6. washeluting with hexanes/EtOAc (2:1)

Sources & evidence

ORD record
ord-fb1f702bba2644399c47a9467924525a
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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