Water → HCID 53353683, compound

HRID 2174529Notes

Reaction equation

HRID 2174529 reaction equation
[Cl:1][C:2]1[C:3](=[O:19])[N:4]([CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:5]=[CH:6][C:7]=1Cl.[CH3:20][NH2:21].O>CS(C)=O>[Cl:1][C:2]1[C:3](=[O:19])[N:4]([CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:5]=[CH:6][C:7]=1[NH:21][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 53353682HCID 53353682, compound

Product 1

HCID 53353683HCID 53353683, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dichloro-2-(3,3,5,5-tetramethylcyclohexyl)pyridazin-3-one (0.3 g, 1.475 mmoles) was dissolved in DMSO (20 mL) and a 40% aqueous solution of methylamine (0.6 mL, 1.7 mmoles) was added with stirring. Heated at 100° C. overnight. Allowed to cool and then poured into water. A solid precipitated out and was filtered off. Purified using a silica cartridge eluted with ethyl acetate:isohexane (3:7) to give the product as a cream solid (150 mg). 1H NMR (300 MHz CDCl3) 7.65 (s, 1H), 5.35 (m, 1H), 4.7 (brs, 1H), 3.05 (d, 3H, J=5 Hz), 1.55 (m, 4H), 1.3 (m, 1H), 1.15 (m, 1H), 1.15 (s, 6H), 0.95 (s, 6H).

Workup

  1. temperatureAllowed to cool
  2. customA solid precipitated out and
  3. filtrationwas filtered off
  4. customPurified
  5. washeluted with ethyl acetate:isohexane (3:7)

Sources & evidence

ORD record
ord-7fdfa777e5164df69e1e6a5e6b50d23b
Source dataset
uspto-grants-2015_06
Patent number
US09062004B2

Reaction notes

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