p-Toluenesulfonic acid → N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride

HRID 596231Notes

Reaction equation

HRID 596231 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].[ClH:16].[CH:17]1([NH:23][CH:24](O)[CH3:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[ClH:16].[CH3:25][CH2:24][N:23]([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:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 83573,4,5-Trimethoxybenzoic AcidHCID 20534156Cyclohexylamino-ethanol-hydrochloride

Product 1

HCID 88821243N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.0 g of 3,4,5-trimethoxy-benzoic acid, 1.8 g. of cyclohexylamino-ethanol-hydrochloride and 4.0 g. of p-toluene-sulphonic acid are refluxed in 40 ml. of benzene for 12 hours. After cooling the reaction mixture is extracted with a 15% sodium carbonate solution and 10% hydrochloric acid. White crystals precipitate from the hydrochloric acid solution. Thus N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride is obtained. Mp.: 207°-208° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionis extracted with a 15% sodium carbonate solution and 10% hydrochloric acid
  3. customWhite crystals precipitate from the hydrochloric acid solution

Sources & evidence

ORD record
ord-149f655c77f34aeca4d75bdad0a91374
Source dataset
uspto-grants-1977_03
Patent number
US04010193

Reaction notes

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