4-[(Methylsulfonyl)amino]benzoyl chloride → HCID 20225364, compound

HRID 1249194Notes

Reaction equation

HRID 1249194 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:12])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[NH2:15][CH2:16][CH2:17][N:18]1[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]1([CH3:27])[CH3:26]>O1CCCC1>[ClH:12].[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:15][CH2:16][CH2:17][N:18]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]2([CH3:27])[CH3:26])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 117911194-[(Methylsulfonyl)amino]benzoyl chlorideHCID 13222167HCID 13222167, compound

Product 1

HCID 20225364HCID 20225364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.72 g (11.1 mmole) of 4-[(methylsulfonyl)amino]benzoyl chloride in 50 ml of tetrahydrofuran cooled to 0° C. under an N2 atmosphere add dropwise 2.04 g (11.1 mmole) of N-(2-aminoethyl)-2,2,6,6-tetramethylpiperidine. After the addition is complete, allow the reaction to stir at ambient temperature overnight. Monitor the progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide;9:1). When the reaction is complete, remove the solvent in vacuo. Dissolve the resulting oil in 50 ml of water. Add 50% sodium hydroxide until pH=14. Wash aqueous with 3×50 ml of diethyl ether. To aqueous layer add concentrated hydrochloric acid until pH=9. Extract with 3×50 ml of methylene chloride. Combine extracts and dry over sodium sulfate. Remove solvent in vacuo. Dissolve resulting oil in methanol and bubble hydrogen chloride gas through the solution until pH 1 is reached. Remove the solvent in vacuo. Recrystallize the solid in methanol/ethyl acetate to provide the title compound.

Workup

  1. additionAfter the addition
  2. customthe reaction
  3. customMonitor the progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide;9:1)
  4. customremove the solvent in vacuo
  5. dissolutionDissolve the resulting oil in 50 ml of water
  6. additionAdd 50% sodium hydroxide until pH=14
  7. additionTo aqueous layer add concentrated hydrochloric acid until pH=9
  8. extractionExtract with 3×50 ml of methylene chloride
  9. dry with materialCombine extracts and dry over sodium sulfate
  10. dissolutionDissolve
  11. customresulting oil in methanol
  12. custombubble hydrogen chloride gas through the solution until pH 1
  13. customRemove the solvent in vacuo
  14. customRecrystallize the solid in methanol/ethyl acetate

Sources & evidence

ORD record
ord-d7b7ea7862ba4502900b3ab437455fa9
Source dataset
uspto-grants-1986_12
Patent number
US04629739

Reaction notes

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