N-Methylaniline → HCID 131716524, compound

HRID 1710111Notes

Reaction equation

HRID 1710111 reaction equation
[CH3:1][O:2][C:3]1([C:14](=[O:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:4]1[CH:5]([OH:9])[C:6]([OH:8])=O.S(Cl)(Cl)=O.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.O.C1(C)C=CC=CC=1>[CH3:21][N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6](=[O:8])[CH:5]([CH:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1([O:2][CH3:1])[C:14](=[O:16])[CH3:15])[OH:9]

Participants

9

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 131716525HCID 131716525, compound

Product 1

HCID 131716524HCID 131716524, compoundYield 95.4%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

22.4 g (0.1 mol) of 2-methoxy-0-acetylmandelic acid were heated under reflux with 100 ml of toluene and 28.8 ml (0.4 mol) of thionyl chloride in the presence of 2 drops of DMF for 2.5 hours. The excess thionyl chloride and the solvent were removed by distillation in vacuo. The residue was dissolved in 25 ml of methylene chloride. To this solution of the acid chloride were added dropwise 10.7 g of N-methylaniline (0.1 mol) and 13.8 ml (0.1 mol) of triethylamine in 100 ml of methylene chloride within 30 minutes. The reaction mixture is left to stand overnight and then 100 ml of water are added. The phases are separated, and the organic phase is washed successively with 50 ml each of 1 N HCl, saturated NaHCO3 solution and water. After drying with anhydrous magnesium sulfate, the solvent is evaporated in vacuo, and the residue is triturated with diisopropyl ether and is filtered off with suction. 30.1 g of crystals of melting point 84°-86° C. are obtained. H NMR (CDCl3): δ=6.4-7.5 (m,9H), 6.23 (s,1H), 3.27 (s,3H), 3.2 (s,3H), 2.08 (s,3H).

Workup

  1. customThe excess thionyl chloride and the solvent were removed by distillation in vacuo
  2. dissolutionThe residue was dissolved in 25 ml of methylene chloride
  3. waitThe reaction mixture is left
  4. customThe phases are separated
  5. washthe organic phase is washed successively with 50 ml each of 1 N HCl, saturated NaHCO3 solution and water
  6. dry with materialAfter drying with anhydrous magnesium sulfate
  7. customthe solvent is evaporated in vacuo
  8. customthe residue is triturated with diisopropyl ether
  9. filtrationis filtered off with suction

Sources & evidence

ORD record
ord-6bdd207862484bf0b9709976b56fd509
Source dataset
uspto-grants-1990_08
Patent number
US04952598

Reaction notes

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