Toluene → HCID 88821252, compound

HRID 596234Notes

Reaction equation

HRID 596234 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].S(Cl)([Cl:18])=[O:17].Cl.C1([C:27]([NH2:30])(O)[CH3:28])CCCCC1.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[ClH:18].[OH:17][CH2:28][CH2:27][N:30]([C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:6]([OH:8])=[O:7])[CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 83573,4,5-Trimethoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 21451105HCID 21451105, compound

Product 1

HCID 88821252HCID 88821252, compound

Procedure

To 2.12 g. of 3,4,5-trimethoxy-benzoic acid 10 ml. of toluene and 1.19 g. of thionyl chloride are added and the reaction mixture is refluxed until no more gas evolves. A suspension of 1.8 g. of cyclohexyl aminoethanol-hydrochloride and 3 ml. of toluene are added to the solution thus obtained and the reaction mixture is refluxed until the gas development ceases. After cooling the precipitated crystals are filtered by suction washed with anhydrous ethanol and recrystallized from 96% ethanol under clarifying with activated charcoal. Thus N-2-hydroxyethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride is obtained. Mp: 210° C.

Workup

  1. temperaturethe reaction mixture is refluxed until no more gas evolves
  2. additionA suspension of 1.8 g
  3. customthus obtained
  4. temperaturethe reaction mixture is refluxed until the gas development ceases
  5. temperatureAfter cooling the precipitated crystals
  6. filtrationare filtered by suction
  7. washwashed with anhydrous ethanol
  8. customrecrystallized from 96% ethanol

Sources & evidence

ORD record
ord-09ad149bf864489db8b548defb3a7eab
Source dataset
uspto-grants-1977_03
Patent number
US04010193

Reaction notes

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