Dimethylformamide → 5-(3-Aminocrotonyl)-2-methylthiazolidine 1,1-dioxide
Reaction equation
[NH2:1][C:2]([CH3:12])=[CH:3][C:4](=[O:11])[CH2:5][S:6](NC)(=[O:8])=[O:7].[CH2:13](Br)[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+].[CH3:23][N:24](C)C=O>>[NH2:1]/[C:2](/[CH3:12])=[CH:3]\[C:4]([CH:5]1[S:6](=[O:7])(=[O:8])[CH:13]([CH3:14])[NH:24][CH2:23]1)=[O:11]Participants
5
Procedure
In accordance with the procedure described in Example 7, a solution of 3.8 g of 4-amino-N-methyl-2-oxo-3-pentenesulfonamide and 4 ml of ethylene bromide in 50 ml of dimethylformamide were treated with 12 g of potassium carbonate and the mixture was stirred intensively at 80° in an oil bath for 6 hours. The product was firstly chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (1:1) as the elution agent and then recrystallized from ethanol. There were obtained 1.9 g of 5-(3-aminocrotonyl)-2-methylthiazolidine 1,1-dioxide in the form of colorless crystals, m.p. 113°-115°.
Workup
- customThe product was firstly chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (1:1) as the elution agent
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-7140e06332484946a9db9dfcb5526d8c
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04742069
Reaction notes
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