Hydrochloric Acid → HCID 18541420, compound

HRID 1637907Notes

Reaction equation

HRID 1637907 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10][N+:11]([O-:13])=[O:12])=[O:9])=[C:4]([Cl:14])[CH:3]=1.N1C=CC=CC=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>O.C1COCC1>[Cl:14][C:4]1[CH:3]=[C:2]([NH:1][S:28]([C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH:7]=[CH:6][C:5]=1[C:8]([CH2:10][N+:11]([O-:13])=[O:12])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 18541408HCID 18541408, compound

Product 1

HCID 18541420HCID 18541420, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture composed of 2 g (9.3 mmol) of the amine obtained in Example 13, 1.5 ml (18.5 mmol) of pyridine, 2.95 g (13.9 mmol) of 4-chlorobenzenesulfonic acid chloride and 80 ml of THF is heated for 16 h at 40° C. After cooling, 100 ml of water and 5 ml of concentrated hydrochloric acid are added before extracting with ethyl acetate. The organic phase is washed with a dilute sodium hydroxide solution. This aqueous phase is then acidified with HCl and extracted with ethyl acetate, which is then washed with water until neutral, dried over Na2SO4 and concentrated under vacuum. The residue is purified by chromatography on a silica column in a dichloromethane/methanol (98:2) mixture.

Workup

  1. temperatureAfter cooling
  2. extractionbefore extracting with ethyl acetate
  3. washThe organic phase is washed with a dilute sodium hydroxide solution
  4. extractionextracted with ethyl acetate, which
  5. washis then washed with water until neutral,
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified by chromatography on a silica column in a dichloromethane/methanol (98:2) mixture

Sources & evidence

ORD record
ord-edcd88c76a7a45319d89a25915bf10f3
Source dataset
uspto-grants-2000_03
Patent number
US06043281

Reaction notes

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