Acetyl chloride → N-acetyl-o-toluidine

HRID 1675323Notes

Reaction equation

HRID 1675323 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:18])[CH3:17]>>[C:16]([NH:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 6367Acetyl chloride2×HCID 7242O-ToluidineHCID 8471Triethylamine

Product 1

HCID 8443N-acetyl-o-toluidineYield 67,384.602%

Conditions

Temperature
2.5 °C

Procedure

Ortho toluidine (0.75 mol, 80 grams) was taken in a 1 L round bottom flask equipped with a liquid addition funnel and a guard tube. Triethylamine (1.13 mmol, 113.77 grams) was added to it in one lot. Above mixture was cooled to 0-5° C. and acetyl chloride (1.13 mmol, 88.7 grams) was added drop wise by maintaining the temperature below 10° C. After addition of acetyl chloride, cooling was removed and the reaction mass was stirred at 25-28° C. for a period of 3 hours. After completion of the reaction, the reaction mixture was poured onto 500 grams of ice-water and 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 of solid product.

Workup

  1. customequipped with a liquid addition funnel and a guard tube
  2. temperatureby maintaining the temperature below 10° C
  3. temperaturecooling
  4. customwas removed
  5. customAfter completion of the reaction
  6. extractionextracted with dichloromethane (2×300 mL)
  7. washThe combined dichloromethane extracts were then washed with water, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe volatiles were removed under the reduced pressure

Sources & evidence

ORD record
ord-e0c799e5157c4fa48bfc1333e34c321e
Source dataset
uspto-grants-2011_08
Patent number
US08003670B2

Reaction notes

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