Ammonia → HCID 22609937, compound

HRID 2306582Notes

Reaction equation

HRID 2306582 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[N:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1.[CH3:14][C:15]1(C(O)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].N>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:6][C:7]1[N:8]=[N:9][C:10]([Cl:13])=[CH:11][C:12]=1[C:15]1([CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 62648Ammonium PersulfateHCID 673313,6-DichloropyridazineHCID 707441-Methylcyclohexanecarboxylic acid

Product 1

HCID 22609937HCID 22609937, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Procedure

Concentrated sulphuric acid (10.7 ml, 0.2 mol) was added to a solution of 3,6-dichloropyridazine (10 g, 67 mmol) in water (250 ml). This mixture was heated to 70° C. before addition of 1-methylcyclohexane carboxylic acid (9.67 g, 68 mmol). Silver nitrate (2.3 g, 13.5 mmol) in water (5 ml) was then added over one minute followed by ammonium persulphate (45.6 g, 0.2 mol) in water (95 ml) added over 20 minutes. Upon complete addition, the reaction was stirred for an additional 5 minutes and then allowed to cool to room temperature. The mixture was cooled to 0° C. (ice/water bath) and basified with concentrated aqueous ammonia solution (internal temperature <10° C.). The aqueous phase was extracted with dichloromethane (3×350 ml) and the combined extracts washed with brine (350 ml), dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica using 0→5% ethyl acetate in dichloromethane as eluent to give the required product (5.93 g): 1H NMR (250 MHz, CDCl3) δ 1.33-1.74 (6H, m), 1.43 (3H, s), 1.80-1.96 (2H, m), 1.97-2.12 (2H, m), 7.49 (1H, s); MS (ES+) m/e 249 [MH]+, 247 [MH]+, 245 [MH]+.

Workup

  1. additionadded over 20 minutes
  2. additionUpon complete addition
  3. extractionThe aqueous phase was extracted with dichloromethane (3×350 ml)
  4. washthe combined extracts washed with brine (350 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica using 0→5% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-79cde73cbc71481d93a69a10b13f30ca
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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