Dichloromethane → 2-[(4-methylbenzoyl)amino]benzamide

HRID 1388235Notes

Reaction equation

HRID 1388235 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(Cl)Cl.C(N(CC)CC)C.[C:21]1([CH3:30])[CH:26]=[CH:25][C:24]([C:27](Cl)=[O:28])=[CH:23][CH:22]=1>O>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:30])=[CH:22][CH:23]=1)=[O:28])(=[O:9])[NH2:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6942AnthranilamideHCID 8471TriethylamineHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 8196472-[(4-methylbenzoyl)amino]benzamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well stirred mixture of anthranilamide (34.05 g; 0.25 mol), methylene chloride (650 ml) and triethylamine (~30 ml) is added p-toluoyl chloride (33 ml; 0.25 mol) dropwise over 25 minutes (a slight exotherm is noted). On completion of the addition, the reaction mixture is stirred for one hour, diluted with water (1000 ml). The mixture is stirred vigorously, filtered, the product washed with water and dried to afford 56.08 g solid, mp 206°-208° C.

Workup

  1. additionOn completion of the addition
  2. stirringthe reaction mixture is stirred for one hour
  3. stirringThe mixture is stirred vigorously
  4. filtrationfiltered
  5. washthe product washed with water
  6. customdried

Sources & evidence

ORD record
ord-b9a99c6619c74900803ce805d66cd394
Source dataset
uspto-grants-1984_02
Patent number
US04431440

Reaction notes

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