Toluene → HCID 19844949, compound

HRID 2351998Notes

Reaction equation

HRID 2351998 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(OCC)(=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[S:32]([CH3:31])(=[O:34])=[O:33])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 19844856HCID 19844856, compound

Product 1

HCID 19844949HCID 19844949, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 3.2 g. portion of 3-(3-nitrophenylaminomethyl)pyridine was dissolved in 15 ml. of toluene, and 2.7 g. of potassium carbonate and 1.6 ml. of methanesulfonyl chloride were added. The mixture was heated to a gentle boil and stirred overnight under reflux. Twenty-five ml. of water and 25 ml. of ethyl acetate were added, and the organic phase was dried and evaporated under vacuum. The residue was triturated with diethyl ether, filtered and dried to obtain 2.4 g. of the desired product, m.p. 131°-133°.

Workup

  1. temperatureThe mixture was heated to a gentle boil
  2. temperatureunder reflux
  3. customthe organic phase was dried
  4. customevaporated under vacuum
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered
  7. customdried
  8. customto obtain 2.4 g

Sources & evidence

ORD record
ord-373f5becdfac4082a851f146f101ff2c
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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