Ethylene Glycol → HCID 12275053, compound

HRID 1730652Notes

Reaction equation

HRID 1730652 reaction equation
[NH2:1][C:2]1[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[C:3]=1[C:4](NNS(C1C=CC=CC=1)(=O)=O)=O.[N:29]12[CH2:36][CH2:35]N([CH2:33][CH2:34]1)CC2.[C:37](=[O:40])([O-])[O-].[Na+].[Na+].O.[CH2:44](O)[CH2:45]O>C(O)(=O)C>[N:29]1[CH:34]=[CH:33][C:44]([C:45]2[C:37](=[O:40])[NH:1][C:2]3[C:3]([CH:4]=2)=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[N:20]=3)=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 962WaterHCID 9237DabcoHCID 10340Sodium CarbonateHCID 12275049HCID 12275049, compound

Product 1

HCID 12275053HCID 12275053, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glycol (30 ml.) is heated in a oil-bath at 175° C. N1 -[2-amino-4,6-di(trifluoromethyl)-nicotinoyl]-N2 -benzenesulfonyl hydrazine (1.28 g., 3 mmole) is added followed immediately by a solution of methyl 4-pyridyl acetate (453 mg., 3 mmole) and 1,4-diazabicyclo[2,2,2]octane (336 mg., 3 mmole) in ethylene glycol (6 ml.). The mixture is stirred vigorously until the temperature reaches 160° C. whereupon anhydrous sodium carbonate (900 mg.) is added. Heating in the oil-bath is continued for one minute and the reaction mixture then is allowed to cool and is then poured into water (200 ml.). Precipitation of the product is initiated by the addition of a single drop of acetic acid. A fine ochre colored solid is collected after it crystallizes overnight giving 639 mg. of product, m.p. 235°-236° C. Neutralization of the mother liquors to pH 7 with acetic acid provides an additional 51 mg. of product, m.p. circa 250°-270° C. Purification of the combined crude material by soxhlet extraction with acetonitrile gives 328 mg. (30%) of product., m.p. 282°-285° C. with some decomposition.

Workup

  1. additionis added
  2. temperatureHeating in the oil-bath
  3. temperatureto cool
  4. customPrecipitation of the product
  5. additionis initiated by the addition of a single drop of acetic acid
  6. customA fine ochre colored solid is collected after it
  7. customcrystallizes overnight
  8. customgiving 639 mg
  9. customPurification of the
  10. extractionby soxhlet extraction with acetonitrile
  11. customgives 328 mg

Sources & evidence

ORD record
ord-db950587c46f4ff290df49f384946119
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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