5-Methylisoxazol-3-amine hydrochloride → HCID 178428595, compound

HRID 1679368Notes

Reaction equation

HRID 1679368 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[C:9]([NH:11][C:12]([NH2:14])=[NH:13])#[N:10]>C(O)CCC>[ClH:1].[CH3:8][C:6]1[O:5][N:4]=[C:3]([NH:2][C:9]([NH:11][C:12]([NH2:14])=[NH:13])=[NH:10])[CH:7]=1

Participants

4

Reactant 2

HCID 203177225-Methylisoxazol-3-amine hydrochlorideHCID 178418324HCID 178418324, compound

Product 1

HCID 178428595HCID 178428595, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a 2 liter three-necked flask are added 370 g of 3-amino-5-methyl-isoxazole hydrochloride, 231 g of 1-cyano-guanidine and 500 ml of butanol. The temperature is gradually raised to the refluxing temperature of the solvent, at which level it is then maintained during 10 minutes. The reaction mixture is allowed to cool and, after incipient crystallization, is poured over 2 liters of butanol. After complete crystallization, the resulting material is filtered, the solid is washed with 300 ml of isopropanol. The solid is recrystallized from 1 liter 90% ethanol, to give 250 g of (5-methyl-isoxazol-3-yl)biguanide hydrochloride. M.p. (Kofler) = 210°-212° C. M.p. (cap.) = 195°-196° C with introduction at 185° C and heating at a rate of 2° C/minute.

Workup

  1. temperatureThe temperature is gradually raised to the refluxing temperature of the solvent, at which level it
  2. temperatureis then maintained during 10 minutes
  3. temperatureto cool
  4. customafter incipient crystallization
  5. additionis poured over 2 liters of butanol
  6. customAfter complete crystallization
  7. filtrationthe resulting material is filtered
  8. washthe solid is washed with 300 ml of isopropanol
  9. customThe solid is recrystallized from 1 liter 90% ethanol

Sources & evidence

ORD record
ord-7ec9f9d6d7d74953a4f63238bf7a8a26
Source dataset
uspto-grants-1978_03
Patent number
US04080460

Reaction notes

Loading…