Reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].CCCC[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-:16].[Na+].[H][H].[C:20]([Cl:23])(Cl)=O.[NH3:24].[CH2:25]1CCCCC1>[Pd]>[Cl:23][CH2:20][CH2:25][O:16][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[S:2]([NH2:24])(=[O:5])=[O:3]Participants
Procedure
A process according to claim 1, wherein the compound of formula II is reacted with ethylene carbonate in the presence of a catalytic amount of tributylamine at a temperature between +130° C. and +150° C.; the resulting reaction mixture is treated with phosgene in the presence of a catalytic amount of dimethylformamide at a temperature between +70° C. and +90° C. yielding the compound of formula IV, which after purification is treated with 1 equivalent of chlorosulfonic acid or with a slight excess thereof in cyclohexane or n-decane at a temperature between +20° C. and +60° C.; neutralized with aqueous sodium hydroxide at a temperature between +50° C. and +90° C.; dechlorinated with hydrogen in the presence of an acid acceptor, in the pressure range from 1 to 5 bar at a temperature between +20° C. and +70° C. and in the presence of a 5% palladium on carbon catalyst; converted to the sulfonic acid chloride by treatment of the mixture with phosgene at a temperature between +60° C. and +120° C.; and subsequently reacted to the final product by treatment of the reaction mixture with an aqueous solution of ammonia.
Workup
- customafter purification
- customat a temperature between +20° C. and +60° C.
Sources & evidence
- ORD record
- ord-dba526094804483395f13c80f0fc0217
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806528
Linked notes
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