Benzenesulfonyl chloride → HCID 14989650, compound

HRID 1199676Notes

Reaction equation

HRID 1199676 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[N:6][CH:7]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:14]1([S:20]([NH:1][C:2]2[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[N:6][CH:7]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 13094268HCID 13094268, compound

Product 1

HCID 14989650HCID 14989650, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-amino-2-(3-cyanopropyl)-3-methylpyridine* (5 g) in chloroform (50 ml) was treated with benzenesulphonyl chloride (7.35 ml) and triethylamine (3 ml) for 96 hours. The chloroform layer was extracted with dilute sodium hydroxide solution (2×50 ml). The chloroform layer was discarded and the combined aqueous extracts were adjusted to pH=5 and extracted with chloroform (3×50 ml). The combined extracts were dried over magnesium sulphate, the solvent was removed and the residue was chromatographed on silica gel eluted with 2% v/v methanol in chloroform to give the title compound (3.28 g) as white prisms. m.p. 119°-120° C.

Workup

  1. extractionThe chloroform layer was extracted with dilute sodium hydroxide solution (2×50 ml)
  2. extractionextracted with chloroform (3×50 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulphate
  4. customthe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with 2% v/v methanol in chloroform

Sources & evidence

ORD record
ord-1a64a123fcf447a68725275a85d3c253
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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