Dimethylformamide → HCID 3358379, compound

HRID 393494Notes

Reaction equation

HRID 393494 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.CN(C=O)C.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]>O>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7242O-ToluidineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 3358379HCID 3358379, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3.000 g (16.65 mmol) of 4-acetoxybenzoic acid and 5 ml of thionyl chloride were mixed together and stirred for two hours at 50° C. after the addition of a drop of DMF. After thionyl chloride was removed by distillation under the reduced pressure, 5 ml of NMP was added in an ice bath. After stirring for 10 minutes in the ice bath after the addition of 1.784 g (16.65 mmol) of 2-aminotoluene, then the solution was poured into 400 ml of iced water. Precipitate formed was thoroughly washed to yield 3.634 g of 4-acetoxy-2′-methylbenzanilide shown in the structural formula 9 above in colorless solid (Yield: 81.04%).

Workup

  1. customAfter thionyl chloride was removed by distillation under the reduced pressure, 5 ml of NMP
  2. additionwas added in an ice bath
  3. stirringAfter stirring for 10 minutes in the ice bath
  4. customPrecipitate formed
  5. washwas thoroughly washed

Sources & evidence

ORD record
ord-5d27ca2c74644c6b91aede88fc2f1fe4
Source dataset
uspto-grants-2004_10
Patent number
US06808766B1

Reaction notes

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