Ethyl benzenesulfonate → HCID 21435413, compound

HRID 2398300Notes

Reaction equation

HRID 2398300 reaction equation
[OH:1][C:2]1[C:18]([Cl:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:3]=1[CH2:4][N:5]([CH3:14])[CH:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:21][CH2:22][O-].[Na+].[Na].C(OS(C1C=CC=CC=1)(=O)=O)C>C(O)C.CCOCC>[ClH:19].[CH2:21]([O:1][C:2]1[C:18]([Cl:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:3]=1[CH2:4][N:5]([CH3:14])[CH:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:22]

Participants

7

Reactant 4

HCID 10585Ethyl benzenesulfonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21435401HCID 21435401, compound

Product 1

HCID 21435413HCID 21435413, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

7.4 g of 2-hydroxy-3-chloro-5-methyl-N-methyl-N-cyclooctylbenzylamine were dissolved in 40 ml of hot absolute ethanol and added to a sodium ethylate solution that had been prepared from 0.6 g of sodium in 25 ml of absolute ethanol. After addition of 4.5 g of benzenesulfonic acid ethyl ester, the whole was stirred for 5 hours under reflux, concentrated, the residue was dissolved in 50 ml of 5% sodium hydroxide solution, extracted with ether and the organic phase was dried over sodium sulfate. The solvent was removed and after addition of 70 ml of water and hydrochloric acid until acid reaction the residue was covered with 50 ml of ether and allowed to stand for several days at 0° C. In this manner, 6 g of 2-ethoxy-3-chloro-5-methyl-N-methyl-N-cyclooctyl-benzylamine-hydrochloride were obtained. Melting point 197° C (ethanol/ether).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in 50 ml of 5% sodium hydroxide solution
  4. extractionextracted with ether
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customThe solvent was removed
  7. additionafter addition of 70 ml of water and hydrochloric acid
  8. customuntil acid reaction the residue
  9. waitto stand for several days at 0° C

Sources & evidence

ORD record
ord-4d53986677f0414b955970860bd261fe
Source dataset
uspto-grants-1977_05
Patent number
US04024274

Reaction notes

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