Reaction equation
[CH:1]1([NH:7][S:8](Cl)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:18]([NH:22][C:23](=[NH:26])[O:24][CH3:25])([O:20][CH3:21])=[O:19]>C(OCC)(=O)C>[C:18]([NH:22][C:23](=[N:26][S:8](=[O:10])(=[O:9])[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[O:24][CH3:25])([O:20][CH3:21])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
59.6 parts of cyclohexylaminosulfonyl chloride and 26.9 parts of pyridine were introduced through two feed lines, into a stirred solution of 39.6 parts of N-carbomethoxy-O-methylisourea in 300 parts of ethyl acetate, at from 15° to 20° C. After having been stirred for 4 hours at 25° C., the reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid and was then dried and concentrated under reduced pressure. This gave 79 parts of N-carbomethoxy-N'-cyclohexylsulfamyl-O-methylisourea, of nD25 =1.4970. After trituration with a small amount of ether, the compound crystallized, and these crystals melted at 84°-86° C. 15 parts of this product were dissolved in a mixture of 9 parts of 50% strength by weight sodium hydroxide solution and 20 parts of water and the reaction solution was stirred for 4 minutes at from 55° to 60° C. It was then cooled, extracted once with ether, and stirred into a mixture of 9.5 parts of concentrated hydrochloric acid and 10 parts of water. Filtering off the product, washing with water and drying gave 9 parts of 6-cyclohexyl-3-methoxy-5,6-dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxide, of melting point 173°-177° C. This constitutes active compound No. 3.
Workup
- extractionthe reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid
- customwas then dried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-40f32790c28b4cde9e46c6107d3e6d29
- Source dataset
- uspto-grants-1982_02
- Patent number
- US04316014
Linked notes
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