Hydrogen Bromide → 2-(2-Dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethylamine
Reaction equation
C([CH:3]([C:5]1[N:6]=[C:7]([CH2:11][N:12]([CH3:14])[CH3:13])[S:8][C:9]=1[CH3:10])O)C.Cl.[NH2:16][CH2:17][CH2:18][SH:19].Br>>[CH3:14][N:12]([CH2:11][C:7]1[S:8][C:9]([CH3:10])=[C:5]([CH2:3][S:19][CH2:18][CH2:17][NH2:16])[N:6]=1)[CH3:13]Participants
Procedure
Following the procedure of Example 3, a reaction mixture consisting of 6.4 g. of ethyl 2-dimethylaminomethyl-5-methyl-4-thiazolemethanol, 4.2 g. of cysteamine hydrochloride and 30 ml. of 48% aqueous hydrobromic acid was maintained at a temperature of about 100° C. under a nitrogen atmosphere for about 4 hours. The reaction mixture was cooled and the volatile constituents removed in vacuo. The resulting dark residue was twice trituated with ethanol and the ethanol removed by evaporation to remove residual HBr. The residue was then treated with 50 ml. of 5N aqueous sodium hydroxide. The alkaline layer was continuously extracted with ether over an 18 hour period. The ether extract was dried and the ether removed therefrom in vacuo to provide 2-(2-dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethylamine prepared in the above reaction; yield=1.38 g. The compound was a brown oil having the following physical characteristics:
Workup
- temperatureThe reaction mixture was cooled
- customthe volatile constituents removed in vacuo
- customthe ethanol removed by evaporation
- customto remove residual HBr
- additionThe residue was then treated with 50 ml
- extractionThe alkaline layer was continuously extracted with ether over an 18 hour period
- extractionThe ether extract
- customwas dried
- customthe ether removed
Sources & evidence
- ORD record
- ord-52148395b0d34b08bda4385cb39462dc
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04760075
Reaction notes
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