Dimethylamine → HCID 20332977, compound

HRID 1706998Notes

Reaction equation

HRID 1706998 reaction equation
[CH3:1][NH:2][CH3:3].[OH:4][CH:5]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]([CH2:24]Cl)=[N:22][C:21]([C:26]([NH2:28])=[O:27])=[N:20]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I-].[Na+]>CO>[OH:4][CH:5]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]([CH2:24][N:2]([CH3:3])[CH3:1])=[N:22][C:21]([C:26]([NH2:28])=[O:27])=[N:20]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 20333030HCID 20333030, compound

Product 1

HCID 20332977HCID 20332977, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.8 ml of 33% ethanolic dimethylamine solution is added to a solution of 5.6 g (about 0.015 mole) of 1-[2-(α-hydroxybenzyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxamide and 0.225 g of sodium iodide in 80 ml of methanol, and the whole is refluxed for 5 hours with stirring. The reaction mixtute is thereupon concentrated in vacuo. Water and saturated sodium carbonate solution are added to the residue until the pH-value has reached 10, and extraction is performed twice with ethyl acetate. The organic phase is washed with water, and is then extracted three times with 1N hydrochloric acid solution. Sodium carbonate is added to the aqueous acidified extracts until the pH-value of 10 is obtained. The base that has precipitated is taken up in ether; the ether solution is washed twice with water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo to yield amorphous 1-[2-(α-hydroxybenzyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]- 1H-1,2,4-triazole-3-carboxamide. This is converted as follows into the crystalline hydrochloride: the crude base is dissolved in ethyl acetate, and ethereal hydrogen chloride solution is added until the pH-value is 4. The precipitated hydrochloride is filtered off with suction and washed with ethyl acetate and ether. After drying in vacuum, there is obtained 1-[2-(α-hydroxybenzyl) 4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide-hydrochloride, m.p. 155°-157° (with decomposition).

Workup

  1. temperaturethe whole is refluxed for 5 hours
  2. concentrationThe reaction mixtute is thereupon concentrated in vacuo
  3. additionWater and saturated sodium carbonate solution are added to the residue until the pH-value
  4. extraction10, and extraction
  5. washThe organic phase is washed with water
  6. extractionis then extracted three times with 1N hydrochloric acid solution
  7. additionSodium carbonate is added to the
  8. customis obtained
  9. customThe base that has precipitated
  10. washthe ether solution is washed twice with water and once with saturated sodium chloride solution
  11. dry with materialit is dried over sodium sulphate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1756fdb2015a463c8ae093d764f2ba96
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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