Sodium Methoxide → HCID 70074918, compound

HRID 1034172Notes

Reaction equation

HRID 1034172 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[C:17](=O)[CH3:18])(=[O:8])=[O:7].Cl.[CH3:24][O:25][C:26](=[O:31])[CH2:27][C:28](=[NH:30])[NH2:29].C[O-].[Na+]>CO>[CH3:24][O:25][C:26]([C:27]1[CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:8])=[O:7])[C:16]([N+:20]([O-:22])=[O:21])=[C:17]([CH3:18])[NH:29][C:28]=1[NH2:30])=[O:31]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 19988776Methyl 2-Amidinoacetate HydrochlorideHCID 54506574HCID 54506574, compound

Product 1

HCID 70074918HCID 70074918, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3.2 g of 4-{2-[(4-chlorobutyl)sulfonyl]phenyl}-3-nitro-3-buten-2-one in 25 ml of methanol in a 100 ml single-neck flask at 0° C. was added 1.41 g of amidino-acetic acid methyl ester hydrochloride, followed by 2.2 ml of 25% sodium methoxide in methanol. The mixture was warmed to room temperature and stirred overnight. After removal of the methanol, the residue was partitioned between water and dichloromethane. The organic layer was dried over magnesium sulfate and evaporated to give a crude product, which was purified via column chromatography on silica gel, eluting with 60:40 toluene:ethyl acetate. Recrystallization from isopropyl acetate provided 1.08 g of an orange product, m.p. 218° C. 1H-NMR (d6 -DMSO) δ 1.71-1 95(m,4H); 2.45(s,3H); 2.48-2.55(m,2H); 3.34(s,3H); 3.69(m,2H); 6.49(s,1H); 6.87(br s,2H); 7.33-7.44(m,2H); 7.56(t,1H,J=8 Hz); 7.79(d,1H,J=8 Hz); 9.51(br s,1H). Mass spectrum: 444 (M+H).

Workup

  1. customAfter removal of the methanol
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customto give a crude product, which
  6. customwas purified via column chromatography on silica gel
  7. washeluting with 60:40 toluene
  8. customRecrystallization from isopropyl acetate

Sources & evidence

ORD record
ord-58da145735af4164b836d4d39c9778e1
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

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