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

HRID 1199496
Notes
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Reaction equation

HRID 1199496 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].[CH3:11][S:12]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([N:22]2[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)(=[O:14])=[O:13].[OH-].[NH4+].[P:29](=[O:33])([OH:32])([OH:31])[OH:30]>C(#N)C.CO>[P:29](=[O:30])([OH:33])([OH:32])[OH:31].[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:24][CH2:23][NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([NH:15][S:12]([CH3:11])(=[O:13])=[O:14])=[CH:26][CH:25]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 14923Ammonium HydroxideHCID 480381-Heptanamine, N-ethyl-HCID 147735491-[4-[(Methylsulfonyl)amino]benzoyl]aziridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

0.60 g (4.16 mmol) of N-ethylheptanamine and 0.50 g (2.08 mmol) of 1-[4-[(methylsulfonyl)amino]benzoyl]aziridine are dissolved in 10 mL of acetonitrile and the solution is warmed to 50° C. for 48 hours. The reaction is monitored by thin-layer chromatography (silica gel (EM); acetonitrile:conc. ammonium hydroxide (90:10)). After 48 hours, the reaction mixture is evaporated and the resultant solid is dissolved in 20 mL of methylene chloride. This solution is extracted with 2×10 mL of 1N aq. sodium hydroxide. The aqueous extract is acidified to pH=1 with 6N aq. hydrochloric acid and extracted with 2×15 mL of methylene chloride. The combined organic extracts are neutralized with saturated aqueous sodium bicarbonate and washed with 10 mL of water. The organic layer is dried over sodium sulfate, filtered and evaporated on a rotary evaporator to provide an oil. This oil is dissolved in 20 mL of 50% aqueous methanol and titrated to pH=4.5 with 0.1N aq. phosphoric acid. This solution is evaporated on the rotary evaporator and residual water is removed by azeotroping with 20 mL of alcohol. This residue is crystallized from 8 mL of reagent alcohol to provide the title compound.

Workup

  1. customthe reaction mixture is evaporated
  2. dissolutionthe resultant solid is dissolved in 20 mL of methylene chloride
  3. extractionThis solution is extracted with 2×10 mL of 1N aq. sodium hydroxide
  4. extractionThe aqueous extract
  5. extractionextracted with 2×15 mL of methylene chloride
  6. washwashed with 10 mL of water
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated on a rotary evaporator
  10. customto provide an oil
  11. customThis solution is evaporated on the rotary evaporator and residual water
  12. customis removed
  13. customby azeotroping with 20 mL of alcohol
  14. customThis residue is crystallized from 8 mL of reagent alcohol

Sources & evidence

ORD record
ord-05fadfaff5ed49a899736c82fb65c62e
Source dataset
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04900841

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes