Methanol → HCID 13084138, compound

HRID 67257Notes

Reaction equation

HRID 67257 reaction equation
[CH3:1]O.S(Cl)(Cl)=O.[I:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19]([CH3:20])=[CH:18][C:17](=[O:21])[C:16]([C:22]([OH:24])=[O:23])=[N:15]2)=[CH:10][CH:9]=1.O>C(Cl)(Cl)Cl>[I:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19]([CH3:20])=[CH:18][C:17](=[O:21])[C:16]([C:22]([O:24][CH3:1])=[O:23])=[N:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 130841151-(4-Iodophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylic acid

Product 1

HCID 13084138HCID 13084138, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To 50 ml of methanol, cooled to -5°, there is added dropwise 2.62 g (0.022 mol) of thionyl chloride (pot temperature maintained between -5° C. and 0° C.). The solution is stirred at 0° C. for 15 min and to it there is added 7.12 g (0.02 mol) of 1-(4-iodophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylic acid. (See Example 3). The suspension formed is stirred at room temperature for 3 days and to it there is added 200 ml of water. The suspension that forms is stirred at room temperature for 2 days and is vacuum filtered. The filter cake is air dried to afford 4 g of crude product. The crude product is suspended in 25 ml of chloroform and filtered. The filtrate is concentrated in vacuo to afford 3.5 g (47% yield) of product, mp 185°-187° C.

Workup

  1. customThe suspension formed
  2. stirringis stirred at room temperature for 3 days and to it there
  3. stirringThe suspension that forms is stirred at room temperature for 2 days
  4. filtrationfiltered
  5. customdried
  6. customto afford 4 g of crude product
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-172a615ecc1b4e15bfdf3ff7559cc6cb
Source dataset
uspto-grants-1982_08
Patent number
US04345934

Reaction notes

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