Hydrochloric Acid → Tetrahydro-3-methyl-2-(nitromethylene)-1,3-thiazine
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][SH:6].[OH-].[Na+].Cl[C:10](Cl)=[CH:11][N+:12]([O-:14])=[O:13].Cl>CO.C(Cl)Cl.O>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][S:6][C:10]1=[CH:11][N+:12]([O-:14])=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Into 40 ml of methanol were added 5.0 g of 1-methylamino-3-propanethiol and 0.8 g of caustic soda, followed by stirring, to be completely dissolved therein. Then, the mixture was cooled to 0° C. While stirring the solution, a solution of 1.6 g of caustic soda dissolved in 25 ml of methanol and a solution of 2.8 g of 2,2-dichloronitroethylene diluted in 20 ml of methanol were added at the same time dropwise slowly over 50 minutes, and the reaction was carried out for one hour at about 8° C. After the reaction, the reaction mixture was neutralized to pH 7 with 3 N aqueous hydrochloric acid, and then with addition of 60 ml of water, extraction with 50 ml of methylene chloride was repeated four times. The extracts were concentrated to give 3.38 g of tetrahydro-3-methyl-2-(nitromethylene)-1,3-thiazine (yield: 97%).
Workup
- dissolutionto be completely dissolved
- stirringWhile stirring the solution
- additionwere added at the same time dropwise slowly over 50 minutes
- customAfter the reaction
- concentrationThe extracts were concentrated
Sources & evidence
- ORD record
- ord-b92e1cb9685a4fa5a23cdd426fca6e64
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04665172
Reaction notes
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