3-Amino-5-methylisoxazole → HCID 178428571, compound

HRID 1389774Notes

Reaction equation

HRID 1389774 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.Cl.[C:9](=[NH:20])(SCCC)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[CH3:7][C:5]1[O:4][N:3]=[C:2]([NH:1][C:9](=[NH:20])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 20295658HCID 20295658, compound

Product 1

HCID 178428571HCID 178428571, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 1 liter flask provided with a condenser, a thermometer and a stirring device are added 250 ml acetonitrile, 24.5 g 3-amino-5-methyl-isoxazole. This gives a solution to which are added 54 g propyl thiobenzimidate hydrochloride, and the resulting suspension is then refluxed. Dissolution is found to occur. Refluxing is maintained 2 hours. The material crystallizes and is left aside overnight, after which it is filtered, suction filtered and dried. Crystallization from isopropanol and reconversion to the base by addition of the suitable amount of sodium hydroxide solution give 28 g N-(5-methyl-isoxazol-3-yl)-benzamidine. (Yield: 56%). M.p. (capillary tube): 127°-129° C.

Workup

  1. customIn a 1 liter flask provided with a condenser
  2. customThis gives a solution to which
  3. temperaturethe resulting suspension is then refluxed
  4. dissolutionDissolution
  5. temperatureRefluxing
  6. temperatureis maintained 2 hours
  7. customThe material crystallizes
  8. filtrationafter which it is filtered
  9. filtrationsuction filtered
  10. customdried
  11. customCrystallization from isopropanol and reconversion to the base
  12. additionby addition of the suitable amount of sodium hydroxide solution

Sources & evidence

ORD record
ord-94a07967aa3a47288f4f55f132bcb5f8
Source dataset
uspto-grants-1981_01
Patent number
US04246272

Reaction notes

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