Methyl p-toluenesulfonate → HCID 131729225, compound

HRID 1662898Notes

Reaction equation

HRID 1662898 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[CH3:10][O:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[CH3:10])(=[O:3])[CH3:2].[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([OH:14])(=[O:13])=[O:11])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 142862-Acetylpyridine

Product 1

HCID 131729225HCID 131729225, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50.0 g (0.41 mol) of 2-acetylpyridine and 80.6 g (0.43 mol) of p-toluenesulfonic acid methyl ester were refluxed in 250 ml of toluene for 5 hours. After cooling, the light brown solid that had formed was filtered off, rinsed with toluene and dried under vacuum. Yield: 77.2 g (61%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=2.30 (s, 31-1); 2.81 (s, 3H); 4.35 (s, 3H); 7.10 (d, 2H); 7.47 (d, 2H); 8.26 (dd, 1H); 8.61 (d, 1H); 8.78 (dd, 1H); 9.18 (d, 1H).

Workup

  1. temperatureAfter cooling
  2. customthe light brown solid that had formed
  3. filtrationwas filtered off
  4. washrinsed with toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2da2a761f29a4aef955891e162da7178
Source dataset
uspto-grants-2011_10
Patent number
US08034122B2

Reaction notes

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