4-Toluenesulfonyl chloride → HCID 54122358, compound

HRID 1975388Notes

Reaction equation

HRID 1975388 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 53838801HCID 53838801, compound

Product 1

HCID 54122358HCID 54122358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3 g of methyl 6-(4-aminophenyl)-6-(3-pyridyl)-hex-5-enoate, 1.9 g of 4-methylbenzene-sulphonic acid chloride and 5 ml of triethylamine in 100 ml of methylene chloride is stirred for one hour at ambient temperature. The organic phase is washed with water, evaporated down and the residue is purified pyer a silica gel column with ethyl acetate. The product fraction is evaporated down and heated in a mixture of 50 ml of ethanol and 3 ml of 10N sodium hydroxide solution to 50° C. for one hour. The reaction mixture is diluted with water and neutralised by the addition of citric acid. The agueous phase is extracted with ethyl acetate, dried and evaporated down. The residue is recrystallised from ethyl acetate/diisopropylether.

Workup

  1. washThe organic phase is washed with water
  2. customevaporated down
  3. customthe residue is purified pyer a silica gel column with ethyl acetate
  4. customThe product fraction is evaporated down
  5. temperatureheated in a mixture of 50 ml of ethanol and 3 ml of 10N sodium hydroxide solution to 50° C. for one hour
  6. additionThe reaction mixture is diluted with water
  7. additionneutralised by the addition of citric acid
  8. extractionThe agueous phase is extracted with ethyl acetate
  9. customdried
  10. customevaporated down
  11. customThe residue is recrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-f225d4b280ba4ef4976239154c6ceb23
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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