Triethylamine → HCID 20225336, compound

HRID 1249193Notes

Reaction equation

HRID 1249193 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[O:27])=[CH:24][CH:23]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27732004-(2-Aminoethyl)thiomorpholineHCID 117911194-[(Methylsulfonyl)amino]benzoyl chloride

Product 1

HCID 20225336HCID 20225336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 ml of methylene chloride under nitrogen atmosphere add 3.1g (14.3 mmole) of 4-thiomorpholinethanamine and 4.42 g (43.6 mmole) of triethylamine. Stir the mixture at ambient temperature for 1 hour, then cool the mixture to -10° C. To the cooled mixture add slowly 3.67 g (15.1 mmole) of 4-[(methylsulfonyl)amino]benzoyl chloride, keeping the temperature below 5° C. When the addition is complete, allow the reaction mixture to stir at ambient temperature. Monitor the progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Upon completion of the reaction, remove the solvent in vacuo. To the resulting solid add 50 ml of water. To the mixture add 50% sodium hydroxide until pH of 14 is reached. Wash the aqueous layer with 3×50 ml of diethyl ether. Add concentrated hydrochloric acid until a white precipitate forms (pH=8.5). Filter the solid and recrystallize from methanol/ethanol to yield the title compound.

Workup

  1. temperaturecool the mixture to -10° C
  2. customthe temperature below 5° C
  3. additionWhen the addition
  4. stirringto stir at ambient temperature
  5. customMonitor the progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1)
  6. customUpon completion of the reaction
  7. customremove the solvent in vacuo
  8. additionTo the resulting solid add 50 ml of water
  9. additionTo the mixture add 50% sodium hydroxide until pH of 14
  10. washWash the aqueous layer with 3×50 ml of diethyl ether
  11. additionAdd concentrated hydrochloric acid until a white precipitate forms (pH=8.5)
  12. filtrationFilter the solid
  13. customrecrystallize from methanol/ethanol

Sources & evidence

ORD record
ord-1ce19c6f92e64c289e3d8f1aa34f22a5
Source dataset
uspto-grants-1986_12
Patent number
US04629739

Reaction notes

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