Pyridine → HCID 19873457, compound

HRID 466374Notes

Reaction equation

HRID 466374 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:20]1C=CC=C[CH:21]=1>O1CCCC1>[CH3:1][S:2]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:21][N:20]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 6115AnilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 19873457HCID 19873457, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (1.25 g, 10.9 mmol) in 10 ml tetrahydrofuran is added to 2.0 g (9.8 mmol) of the aniline from Step II in 35 ml of dry pyridine over 15 min at less than 5° C. The reaction is stirred in the cold for one hour and then at room temperature for 2 days. Toluene is added and concentrated. Toluene addition and concentration is repeated. Chromatography on silica gel eluting with 1.5% and 2.5% CH3OH-0.5-1% NH4OH--CH2Cl2 gives the title compound.

Workup

  1. waitat room temperature for 2 days
  2. concentrationconcentrated
  3. additionToluene addition and concentration

Sources & evidence

ORD record
ord-f1990b91f0674bc0a414dac1a2d3bdcc
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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