Benzenesulfonyl chloride → HCID 70574288, compound

HRID 1680489Notes

Reaction equation

HRID 1680489 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)=[CH:6]1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:20]1([S:26]([NH:1][CH2:2][CH2:3][CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([CH2:14][C:15]3[NH:19][CH:18]=[CH:17][N:16]=3)=[CH:6]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 70574509HCID 70574509, compound

Product 1

HCID 70574288HCID 70574288, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(3-aminopropyl)-3-(1-imidazolylmethyl)indole (1.27 g) and benzenesulphonyl chloride (0.88 g) in pyridine (15 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was treated with an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate (2×50 ml). The combined extracts were washed with water and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel. The column was first eluted with chloroform to remove a small amount of impurity and then the product was eluted with a mixture of chloroform and methanol (20:1). Evaporation of the product containing fractions gave an oil which crystallised on standing. The product was recrystallised from ethyl acetate containing a trace of methanol to give 1-(3-benzenesulphonylaminopropyl)-3-(1-imidazolylmethyl)indole (0.58 g), m.p. 130°-131° C. Found: C, 63.71; H, 5.58; N, 14.03. C21H22N4O2S requires: C, 63.93; H, 5.62; N, 14.20.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. customevaporated to dryness
  3. additionThe residue was treated with an aqueous solution of sodium bicarbonate
  4. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  5. washThe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated
  8. customthe residue was chromatographed on silica gel
  9. washThe column was first eluted with chloroform
  10. customto remove a small amount of impurity
  11. washthe product was eluted with a mixture of chloroform and methanol (20:1)
  12. customEvaporation of the product
  13. additioncontaining fractions
  14. customgave an oil which
  15. customcrystallised
  16. customThe product was recrystallised from ethyl acetate containing a trace of methanol

Sources & evidence

ORD record
ord-5d633a04d82e479684cd96e89995cb63
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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