Acetamidine monohydrochloride → HCID 12952789, compound

HRID 1577124Notes

Reaction equation

HRID 1577124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([NH:15][C:16]([NH:18][NH2:19])=[O:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.[C:21](=N)(N)[CH3:22].C([O-])(=O)C.[Na+]>O(CCOC)CCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([N:15]3[C:21]([CH3:22])=[N:19][NH:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 517045Sodium AcetateHCID 20455093HCID 20455093, compound

Product 1

HCID 12952789HCID 12952789, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 13 parts of N-[4-(4-methoxyphenyl)-1-piperazinyl]hydrazinecarboxamide, 14.2 parts of ethanimidamide hydrochloride, 12.3 parts of sodium acetate and 95 parts of 1,1'-oxybis[2-methoxyethane] is stirred for 3 hours at 130° C. The reaction mixture is poured onto water and the product is extracted twice with dichloromethane. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 5.1 parts (35%) of 2,4-dihydro-4-[4-(4-methoxyphenyl)-1-piperazinyl]-5-methyl-3H-1,2,4-triazol-3-one; mp. 264.3° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted twice with dichloromethane
  3. customThe combined extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-9e4c1a4fc3eb411f90d176f52e2c4e1c
Source dataset
uspto-grants-1981_09
Patent number
US04287195

Reaction notes

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