Acetyl chloride → N-acetyl-o-toluidine

Temperature

2.5 °C

Ortho toluidine (0.75 moles, 80 g.) was taken in a one liter round bottom flask equipped with a liquid addition funnel and a guard tube. Triethylamine (1.13 moles, 113.77 g.) was added to it in one lot. Above mixture was cooled to 0-5° C. and acetyl chloride was added drop-wise maintaining the temperature below 10° C. After addition of acetyl chloride the cooling was removed and reaction was stirred at 25-28° C. for 3 hours. After the completion of reaction (TLC), the reaction mixture was poured on 500 g. of ice-water, and aqueous layer was extracted with dichloromethane (2×300 mL). The combined dichloromethane extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 113.6 grams solid.

1. customequipped with a liquid addition funnel and a guard tube
2. temperaturemaintaining the temperature below 10° C
3. customwas removed
4. customreaction
5. customAfter the completion of reaction (TLC)
6. additionthe reaction mixture was poured on 500 g
7. extractionof ice-water, and aqueous layer was extracted with dichloromethane (2×300 mL)
8. washThe combined dichloromethane extracts were then washed with water, brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe volatiles were removed under the reduced pressure

ORD record

ord-0b90237e821f46a680019bfac89443fa

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998981B2