Hydrochloric Acid → 2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)thio]ethanamine
Reaction equation
Cl.[C:2]([CH2:21][CH2:22][S:23][CH2:24][CH2:25][NH:26]C=O)([C:5]([C:8]([C:11]([C:14]([C:17]([F:20])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])[F:3].[OH-].[Na+]>C(O)C>[C:2]([CH2:21][CH2:22][S:23][CH2:24][CH2:25][NH2:26])([C:5]([C:8]([C:11]([C:14]([C:17]([F:18])([F:19])[F:20])([F:15])[F:16])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])[F:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Concentrated hydrogen chloride solution (37.5% by weight in water, ten-fold excess) was added to a solution of one equivalent of either C6F13C2H4SCH2CH2NHC(O)H in ethanol at 0° C. (32° F.). The reaction mixture was allowed to warm to ambient temperature while being stirred. After the initial foam formation ceased the reaction mixture was slowly heated and held at reflux temperature for 5 h. The progress of the reaction was monitored via gas chromatography. Upon complete conversion the pH of the solution was brought to 8-10 by carefully adding aqueous sodium hydroxide solution. The crude product separated as the bottom layer and was isolated as a dark brown slightly viscous liquid via a separatory funnel. It was washed with water and dried using molecular sieves (4 angstrom) to give the desired product C6F13C2H4SCH2CH2NH2.
Workup
- temperaturewas slowly heated
- temperatureat reflux temperature for 5 h
- customThe crude product separated as the bottom layer
- customwas isolated as a dark brown slightly viscous liquid via a separatory funnel
- washIt was washed with water
- customdried
Sources & evidence
- ORD record
- ord-4632945dd69942c0b8741e4612a0a91e
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324314B2
Reaction notes
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