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

HRID 1287691Notes

Reaction equation

HRID 1287691 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[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.[K+].[Br-]>CCOCC>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH:16][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 702762-Methylbenzoyl chloride2×HCID 253877Potassium Bromide

Product 1

HCID 185821N-(3-Methoxyphenyl)-2-methylbenzene-1-carboximidic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 15.5 g (0.1 mol) portion of o-methylbenzoyl chloride was added dropwise to a stirred solution of 11.9 g (0.1 mol) of m-methoxyaniline and 10.1 g (0.1 mol) of triethylamine in 250 ml of ether and the resulting solution was cooled. After addition of the o-methylbenzoylchloride, the mixture was stirred at room temperature for an additional 5 hours, and the reaction mixture was washed with water to remove triethylamine hydrochloride. The ether layer was dried over anhydrous sodium sulfate and the ether was removed whereby 23.9 g (99%) of fine white prisms having a melting point of 142°-143° C were obtained. IR cm-1 (KBr-tablet), νNH 3250 (S), νCO 1655(S), 1610(S).

Workup

  1. temperaturethe resulting solution was cooled
  2. washthe reaction mixture was washed with water
  3. customto remove triethylamine hydrochloride
  4. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  5. customthe ether was removed whereby 23.9 g (99%) of fine white prisms
  6. customwere obtained

Sources & evidence

ORD record
ord-1b195d2e17004dafa89683724a68e3c7
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Reaction notes

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