Dimethyl Sulfoxide → HCID 178502854, compound

HRID 2220593Notes

Reaction equation

HRID 2220593 reaction equation
[OH-].[Na+].[OH:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]([NH:24]O)=[NH:23])=[CH:18][C:16]=3[CH:17]=2)=[CH:9][CH:8]=1)=[NH:6].S([O:31][CH3:32])(OC)(=O)=O.[CH3:33]S(C)=O>O>[CH3:33][O:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][O:31][CH3:32])=[NH:23])=[CH:18][C:16]=3[CH:17]=2)=[CH:9][CH:8]=1)=[NH:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178513257HCID 178513257, compound

Product 1

HCID 178502854HCID 178502854, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1 M aqueous NaOH solution (20 mL) was added to a stirred solution of 178 (1.70 g, 5.5 mmol) in DMSO (20 mL). The mixture was cooled and dimethyl sulfate (1.5 mL, 15.9 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 4 hours and then overnight at room temperature, diluted with water (100 mL). The product was separated as a white solid and purified by column chromatography (SiO2, EtOAc, Hexanes) and recrystallized from aq HCl to give 0.4 g (22%): mp 270-271° C. (dec). 1H NMR (DMSO-d6) δ7.96 (s, 1H), 7.94 (d, J=8.2 Hz, 2H), 7.80 (d, J=8.2 Hz, 2H), 7.64 (s, 2H), 7.55 (s, 2H), 6.16 (br, 2H), 6.13 (br, 2H), 3.77 (s, 3H), 3.76 (s, 3H). HPLC (method A) tR 9.41 min (100.0 area %). Anal. (C18H18N4O3.2HCl) C, H, N, Cl.

Workup

  1. temperatureThe mixture was cooled
  2. customThe product was separated as a white solid
  3. custompurified by column chromatography (SiO2, EtOAc, Hexanes)
  4. customrecrystallized from aq HCl
  5. customto give 0.4 g (22%)

Sources & evidence

ORD record
ord-6b9a983b8ee746dea1d76855a91d75f6
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

Loading…