Toluene → Benzamide, 3,5-dichloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

HRID 224424Notes

Reaction equation

HRID 224424 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([O:18][CH3:19])=[C:8]([C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=1)[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:27][CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[CH2:34][CH3:35]>C(OCC)C.O>[CH2:34]([N:30]1[CH2:31][CH2:32][CH2:33][CH:29]1[CH2:28][NH:27][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=[C:6]([Cl:5])[C:7]=1[O:18][CH3:19])[CH3:35]

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 27747503,5-Dichloro-2,6-dimethoxybenzoic Acid

Product 1

HCID 54941Benzamide, 3,5-dichloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

20 ml of thionyl chloride is added to 11.9 g (0.047 mol) of 3,5-dichloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry ethyl ether. To the obtained solution is added dropwise while stirring 6.0 g (0.047 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of ethyl ether. After 30 minutes at room temperature 300 ml of water is added while stirring. The water layer is separated and alkalized with sodium hydroxide solution which is added dropwise while stirring and cooling in ice. The precipitate is collected and washed with water. Yield: 9.0 g, m.p. 120°-21° C.

Workup

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry ethyl ether
  4. additionTo the obtained solution is added dropwise
  5. customThe water layer is separated
  6. additionis added dropwise
  7. stirringwhile stirring
  8. temperaturecooling in ice
  9. customThe precipitate is collected
  10. washwashed with water

Sources & evidence

ORD record
ord-b3b738a827e8417e8e72b8888fb1ea24
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Reaction notes

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