Water → HCID 2797875, compound

HRID 1164505Notes

Reaction equation

HRID 1164505 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH3:1][S:2]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 832754-Pyridineethanamine

Product 1

HCID 2797875HCID 2797875, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulphonyl chloride (3.5 g.) was added slowly to 4-(2-aminoethyl)pyridine (3.6 g.) and triethylamine (3.0 g.) in chloroform (40 ml.). The temperature was maintained below 40° C. during the addition, after which the orange solution was left to stand at room temperature overnight. Water (50 ml.) was then added, the chloroform phase was separated, and the aqueous phase extracted with chloroform (100 ml.). The two chloroform solutions were combined, dried (MgSO4) and taken to dryness in vacuo to give a yellow oil which solidified immediately. This solid was crystallized from ethanol to yield white crystals of 4-(2-methanesulphonamidoethyl)pyridine (1.4 g.).

Workup

  1. temperatureThe temperature was maintained below 40° C. during the addition
  2. waitafter which the orange solution was left
  3. customthe chloroform phase was separated
  4. extractionthe aqueous phase extracted with chloroform (100 ml.)
  5. dry with materialdried (MgSO4)
  6. customto give a yellow oil which
  7. customThis solid was crystallized from ethanol

Sources & evidence

ORD record
ord-780155ae895945a7860c0be2f63f9383
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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