Dichloromethane → HCID 14720274, compound

HRID 2351959Notes

Reaction equation

HRID 2351959 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].[OH-].[Na+].ClCCl>O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[N:11]([CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[S:20]([CH3:19])(=[O:22])=[O:21])[CH3:2]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chloride2×HCID 14720273HCID 14720273, compound

Product 1

HCID 14720274HCID 14720274, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 3.9 g. portion of 3-(2,6-diethylphenylaminomethyl)pyridine was suspended in about 10 ml. of methanesulfonyl chloride, and the mixture stood at ambient temperature for 3 days. It was then diluted with water, and made basic to about pH 10 with aqueous sodium hydroxide. It was extracted twice with 15 ml. portions of ethyl acetate, and the combined organic layers were washed twice with 15 ml. portions of water, and dried. The organic solution was evaporated under vacuum to obtain 4.5 g. of oily product. It was dissolved in ethyl acetate and purified over a short silica gel column in ethyl acetate. The product-containing fractions were combined and evaporated to obtain 3.5 g. of impure product. It was dissolved in 10 ml. of dichloromethane, and to it were added 1.26 ml. of triethylamine and 0.7 ml. of methanesulfonyl chloride. The mixture was stirred at ambient temperature for 3 days, and was then filtered, and the filtrate was evaporated under vacuum. The residue was dissolved in chloroform and purified over a silica gel column, eluting with 19:1 chloroform:methanol. The product-containing fractions were combined and evaporated under vacuum to obtain 3.7 g. of product, which was still only about 60% pure.

Workup

  1. extractionIt was extracted twice with 15 ml
  2. washportions of ethyl acetate, and the combined organic layers were washed twice with 15 ml
  3. dry with materialportions of water, and dried
  4. customThe organic solution was evaporated under vacuum
  5. customto obtain 4.5 g
  6. custompurified over a short silica gel column in ethyl acetate
  7. customevaporated
  8. customto obtain 3.5 g
  9. dissolutionIt was dissolved in 10 ml
  10. filtrationwas then filtered
  11. customthe filtrate was evaporated under vacuum
  12. dissolutionThe residue was dissolved in chloroform
  13. custompurified over a silica gel column
  14. washeluting with 19:1 chloroform
  15. customevaporated under vacuum
  16. customto obtain 3.7 g

Sources & evidence

ORD record
ord-2d2959ec23384ef0bf48d9b3785eb684
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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