Propane sultone → 1-(3-Sulfonylpropyl)-2,5-dimethylpyrazine

HRID 980470

Reaction equation

HRID 980470 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.[CH2:9]1[CH2:15][S:12](=O)(=[O:13])[O:11][CH2:10]1>C(OCC)(=O)C>[S:12](=[CH:15][CH2:9][CH2:10][N:3]1[CH:4]=[C:5]([CH3:8])[N:6]=[CH:7][CH:2]1[CH3:1])(=[O:13])=[O:11]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 312522,5-Dimethylpyrazine

Product 1

HCID 886564641-(3-Sulfonylpropyl)-2,5-dimethylpyrazine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

6.0 g of 2,5-dimethylpyrazine (701) and 7.0 g of 1,3-propane sultone were dissolved in 10 ml of ethyl acetate and heated at 40° C. for 2 days. The resultant solid was then filtered and washed with ethyl acetate giving 7.9 g of product (700). It was recrystallized from propanol/water, m.p. 258°-9°. UV H2O max: 204 (3.94), 290 (3.85). 13C NMR: 159.25, S (C5); 152.47, D (C3); 146.91, S (C2); 136.88, D (C6); 57.84, T (NCH2); 47.94, T (CH2SO3-); 25.42, T (CH2); 21.49, Q, 17.16, Q (ArCH3). 1H NMR: 9.15, S (H3); 8.83, S (H6); 4.77, T (NCH2); 3.09, T (CH2SO3-), 2.90, S, 2.75, S (ArCH3); 2.40, M=5 (--CH2 --).

Workup

  1. filtrationThe resultant solid was then filtered
  2. washwashed with ethyl acetate giving 7.9 g of product (700)
  3. customIt was recrystallized from propanol/water, m.p. 258°-9°

Sources & evidence

ORD record
ord-553f9653a67b4bac9f0e3983fbe4690a
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Linked notes

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