Methane → N-[2-(Ethyl(heptyl)amino)ethyl]-4-[(methylsulfonyl)amino]benzamide phosphoric acid salt

HRID 1249196Notes

Reaction equation

HRID 1249196 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].N#N.[CH2:17]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][NH2:22])[CH3:18].[OH:30][P:31]([OH:34])([OH:33])=[O:32].C>C1COCC1.CCO>[P:31]([OH:34])([OH:33])([OH:32])=[O:30].[CH2:17]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][NH:22][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=1)[CH3:18]

Participants

8

Reactant 5

HCID 297MethaneHCID 947NitrogenHCID 1004Phosphoric AcidHCID 117911194-[(Methylsulfonyl)amino]benzoyl chlorideHCID 13491110N~1~-Ethyl-N~1~-heptylethane-1,2-diamine

Product 1

HCID 19867103N-[2-(Ethyl(heptyl)amino)ethyl]-4-[(methylsulfonyl)amino]benzamide phosphoric acid salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5.66 g (0.024 moles) 4-[(methylsulfonyl)amino]benzoyl chloride in 40 ml THF. Chill the solution on an ice/MeOH bath under a stream of N2. Add dropwise 4.5 g (0.024 moles) N-ethyl-N-heptyl-1,2-ethanediamine to the room temperature for about 24 hours. Follow the progress of the reaction by thin layer chromatography on silica gel (Acetonitrile:MeOH:Ammonia, 85:10:5). At the completion of the reaction, remove the solvents in vacuo. Dissolve the resulting oil in 10% K2CO3 solution and extract with 5×100 ml Et2O. Dry the organics over Na2SO4. Evaporate the solvents to provide an oil. Crude wt: 3.38 g. Dissolve the oil in 25 ml EtOH and acidify with 1.02 g 85% H3PO4. Treat the solution with activated charcoal, filter and evaporate the solvents to provide the title compound. Recrystallize the product from EtOH/Et2O.

Workup

  1. customthe progress of the reaction by thin layer chromatography on silica gel (Acetonitrile:MeOH:Ammonia, 85:10:5)
  2. customAt the completion of the reaction
  3. customremove the solvents in vacuo
  4. dissolutionDissolve the resulting oil in 10% K2CO3 solution
  5. extractionextract with 5×100 ml Et2O
  6. dry with materialDry the organics over Na2SO4
  7. customEvaporate the solvents
  8. customto provide an oil
  9. filtrationfilter
  10. customevaporate the solvents

Sources & evidence

ORD record
ord-bcb5bca2789745679c76bedcf8e6f54d
Source dataset
uspto-grants-1986_12
Patent number
US04629739

Reaction notes

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