Hydrochloric Acid → 6-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one
Reaction equation
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[CH:4]=[N:5][OH:6].ClCl.[OH-].[Na+].Cl.[SH:14][CH2:15][C:16](OCC)=[O:17]>O>[N:5](=[C:4]1[C:3]([CH3:8])([CH3:7])[NH:2][C:16](=[O:17])[CH2:15][S:14]1)[OH:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 41 g α-aminoisobutyraldoxime hydrochloride and 150 ml. of water was charged into a stirred flask and cooled to 0° C. Chlorine was added to the solution at 0° C until 22 g. had been taken up. The reaction mixture was stirred at 0° C for 30 minutes after the chlorine addition. Sodium hydroxide (6 g in 40 ml water) was added with stirring to neutralize the hydrochloric acid, after which a solution of 36 g of ethyl mercaptoacetate and 12 g of sodium hydroxide in 40 ml of water was added rapidly at 5° to 10° C. The mixture was warmed to 25° C and stirred overnight. The solid product was filtered, washed with water then dried at room temperature, to yield 7 g of 2-oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 234°-236° C. An nmr spectrum and m.p. comparison showed the product to be identical with that from Example II.
Workup
- stirringwith stirring
- temperatureThe mixture was warmed to 25° C
- stirringstirred overnight
- filtrationThe solid product was filtered
- washwashed with water
- customthen dried at room temperature
Sources & evidence
- ORD record
- ord-2c8bba0d4cfb46b6b34524da065b0448
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04071627
Reaction notes
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