2-Methylbenzoic acid → N-(3-Methoxyphenyl)-2-methylbenzene-1-carboximidic acid

HRID 1578623Notes

Reaction equation

HRID 1578623 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(N(CC)CC)C.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH:16][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 83732-Methylbenzoic acidHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 24387Phosphorus trichloride

Product 1

HCID 185821N-(3-Methoxyphenyl)-2-methylbenzene-1-carboximidic acidYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 13.6 g (0.1 mol) portion of o-methylbenzoic acid, 10.9 g (0.1 mol) of m-methoxyaniline and 10.1 g (0.1 mol) of triethylamine were dissolved in 250 ml of toluene. A 4.6 g (0.033 mol) amount of phosphorus trichloride was added dropwise to the above solution with stirring at 20°-60°C. After the addition, the reaction mixture was stirred at 80°-90°C for 3 hours. The reaction mixture was cooled and washed with water to remove the triethylamine hydrochloride, and the product was dried over anhydrous sodium sulfate. The toluene was removed to give 22.8 g (95%) of fine white prismatic crystals having a melting point of 142°-143°C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at 80°-90°C for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customto remove the triethylamine hydrochloride
  6. dry with materialthe product was dried over anhydrous sodium sulfate
  7. customThe toluene was removed

Sources & evidence

ORD record
ord-d822b1bcc7744a36ab02d1c96a86304d
Source dataset
uspto-grants-1976_02
Patent number
US03937840

Reaction notes

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