Methanol → m-ethylphenyl-N-methylcyanamide

A suspension of 3-ethylphenylcyanamide (4.65 g, 31.8 mmol) and sodium hydride (2.55 g of 80% NaH in mineral oil suspension, 63.6 mmol of NaH) in dried THF was heated at reflux for 3 hours. The reaction mixture was cooled in an ice bath and methyl iodide (11.28 g, 79.5 mmol) was added dropwise with stirring to the mixture. The reaction mixture was then allowed to stir for 15 hours, followed by the successive addition of MeOH (10 mL). The reaction mixture was then concentrated to dryness to give the crude product. Distilled water (40 mL) was added to this crude product and the aqueous mixture was extracted with CH2Cl2 (4×40 mL). The combined organic extracts were washed with water (3×30 mL) and then dried over MgSO4. The solvent was removed to afford the crude product as an amber syrup. Flash chromatography (SiO2, CH2Cl2) of the crude product afforded 4.2 g (75% yield) of the desired product.

1. temperaturewas heated
2. temperatureat reflux for 3 hours
3. temperatureThe reaction mixture was cooled in an ice bath
4. stirringto stir for 15 hours
5. concentrationThe reaction mixture was then concentrated to dryness
6. customto give the crude product
7. extractionthe aqueous mixture was extracted with CH2Cl2 (4×40 mL)
8. washThe combined organic extracts were washed with water (3×30 mL)
9. dry with materialdried over MgSO4
10. customThe solvent was removed
11. customto afford the crude product as an amber syrup

ORD record

ord-6d2ed468d95141ad88f886c984748f7f

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147063