Antimony pentachloride → HCID 22615656, compound
Reaction equation
Cl.[NH2:2][C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[S:13](Cl)([Cl:16])(=[O:15])=[O:14].[Sb](Cl)(Cl)(Cl)(Cl)Cl>C(#N)C>[Cl:16][S:13]([NH:2][C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)(=[O:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of methyl 1-aminocyclohexane-1-carboxylate HCl salt (4.06 g, 20.9 mmol) in acetonitrile (37 ml) was added sulfuryl chloride (26.2 ml, 326 mmol) and antimony pentachloride (0.17 ml, 2.4 mmol). The reaction was heated at 80° C. using a calcium sulfate drying tube overnight. The reaction was concentrated in vacuo to give methyl 1-(chlorosulfonylamino)cyclohexane-1-carboxylate (85%) as a yellow oil that was used without further purification. This material was converted to N-hydroxy-1-{[4-(4-chlorophenyl)-piperazine-1-sulfonyl]amino}cyclohexane-1-carboxamide by following Examples 2 and Example 13 except that the reaction was heated at 45° C.
Workup
- customovernight
- concentrationThe reaction was concentrated in vacuo
Sources & evidence
- ORD record
- ord-41260f07bc5c4e3da48e2b6cea834dd3
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06143744
Reaction notes
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