Bromide ion → HCID 73750950, compound
Reaction equation
NCCS[C:5](=[N:12]O)C1C=CC=CC=1.N[CH2:15]CCl.[Br-].[Na].[C:20](=[S:29])([NH:27][OH:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:30](O)[CH3:31]>>[CH3:15][N:12]([CH3:5])[CH2:30][CH2:31][S:29][C:20](=[N:27][OH:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
Procedure
The described compounds are also made by methods A and C, in the first of which, for example, S-(2-aminoethyl)benzothiohydroximic acid is made by reacting 2-aminoethyl chloride or bromide with the sodium salt of benzothiohydroxamic acid in the presence of ethanol, as a solvent. Stoichiometric quantities are employed at room temperature and the reaction takes about three hours. A similar reaction may be effected to produce S-(2-dimethylaminoethyl)benzothiohydroximic acid. The hydrohalide salts are made by reaction of a hydrohalic acid, such as HCl or HBr, with the hydroximic acid compound. Following method C, stoichiometric quantities of benzonitrile and 2-aminoethanethiol are reacted in the presence of an excess of hydrochloric acid in a suitable solvent, such as diethyl ether. The product is then reacted with hydroxylamine to convert it to the thiohydroximic acid. Such a reaction may also be undertaken with the dimethylaminoethanethiol starting material to product S-(2-dimethylaminoethyl)benzothiohydroximic acid hydrochloride. The hydrochloride salts then may be converted to the corresponding thiohydroximic acids by treatment with a stoichiometric quantity of base, e.g., sodium carbonate.
Workup
- customare employed at room temperature
- customA similar reaction
Sources & evidence
- ORD record
- ord-27bf9ebdc5eb4d6b8e9293a875d21f3c
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03953590
Reaction notes
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