Methyl Ethyl Ketone → HCID 178492798, compound

HRID 985403Notes

Reaction equation

HRID 985403 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.NC(N)=[S:12].CC(CC)=O>O>[CH3:9][O:8][C:5]1[N:4]=[N:3][C:2]([SH:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 744033-Chloro-6-methoxypyridazineHCID 2723790Thiourea

Product 1

HCID 178492798HCID 178492798, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-6-methoxy-pyridazine (100 g), thiourea (105 g) and ethyl methyl ketone (1.8 L) was prepared and refluxed for three hours. The reaction mixture was then cooled and the supernatant was poured into water and extracted with 1M sodium hydroxide (4×100 mL). The sodium hydroxide solution was washed with ethyl acetate (2×50 mL) and the aqueous extract was acidified with sufficient concentrated hydrochloric acid to lower the pH to 5. The resulting yellow solid was collected and air dried to afford the title compound (24%, 23 g); mp, 198-200° C.

Workup

  1. customwas prepared
  2. temperaturerefluxed for three hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with 1M sodium hydroxide (4×100 mL)
  5. washThe sodium hydroxide solution was washed with ethyl acetate (2×50 mL)
  6. extractionthe aqueous extract
  7. customThe resulting yellow solid was collected
  8. customair dried

Sources & evidence

ORD record
ord-6d4d61da8eaa4532a91f8986adcc5bfa
Source dataset
uspto-grants-2005_03
Patent number
US06872722B2

Reaction notes

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