Dimethylamine → HCID 20332980, compound
Reaction equation
[CH3:1][NH:2][CH3:3].ClC1C=CC=CC=1C([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21]Cl)=[N:19][C:18]([C:23]([OH:25])=[O:24])=[N:17]1)=O.[I-].[Na+].[CH3:32][OH:33]>>[Cl:15][C:13]1[CH:14]=[CH:9][CH:10]=[CH:11][C:12]=1[C:32]([C:11]1[CH:12]=[C:13]([Cl:15])[CH:14]=[CH:9][C:10]=1[N:16]1[C:20]([CH2:21][N:2]([CH3:3])[CH3:1])=[N:19][C:18]([C:23]([OH:25])=[O:24])=[N:17]1)=[O:33]Participants
Procedure
310 ml (0.226 mole) of a 33% ethanolic dimethylamine solution is added to a suspension of 45.0 g (0.11 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid (see DT-OS 2,159,527, page 32) and 0.5 g (0.0033 mole) of sodium iodide in 250 ml of methanol, and the mixture is stirred for 6 hours at room temperature. The clear reaction solution is concentrated in vacuo; the residue is dissolved in 200 ml of water, and 2 N hydrochloric acid solution is slowly added until the pH value of 5 is reached. After 16 hours' standing at 0°-5°, the precipitated aminic acid is filtered off and well washed with water and then with ether. Upon drying, there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxylic acid, m.p. 222°-225° with decomposition.
Workup
- concentrationThe clear reaction solution is concentrated in vacuo
- dissolutionthe residue is dissolved in 200 ml of water
- addition2 N hydrochloric acid solution is slowly added until the pH value of 5
- waitAfter 16 hours' standing at 0°-5°
- filtrationthe precipitated aminic acid is filtered off
- washwell washed with water
- customUpon drying
Sources & evidence
- ORD record
- ord-7db8ef4b99b6477bac369b22abe1ed07
- Source dataset
- uspto-grants-1980_06
- Patent number
- US04209516
Reaction notes
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