Reaction equation
[CH3:1][NH:2][S:3]([C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])(=[O:5])=[O:4].[CH2:19]([C:21]1[O:22][CH2:23][CH2:24][N:25]=1)[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>>[C:6]([S:3]([N:2]([CH2:19][CH2:21][NH2:25])[CH3:1])(=[O:5])=[O:4])([C:7]([C:8]([C:9]([F:10])([F:11])[F:12])([F:13])[F:14])([F:15])[F:16])([F:18])[F:17].[CH3:1][N:2]([CH2:23][CH2:24][NH:25][C:21](=[O:22])[CH2:19][CH3:20])[S:3]([C:6]([F:18])([F:17])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:10])([F:11])[F:12])(=[O:5])=[O:4]Participants
Conditions
- Temperature
- 140 °C
Procedure
C4F9SO2—N(CH3)CH2CH2—NH2 was prepared by the following procedure: N-Methylnonafluorobutanesulfonamide (626 g, 2 moles, 3M Company, St. Paul, Minn.), 2-ethyl-2-oxazoline (198 g, 2 moles, Alfa Aesar, Ward Hill, Mass.), and sodium carbonate (17 g, 0.16 mole, EMD Chemicals, Gibbstown, N.J.) were combined and heated for 16 hours at 140° C. to form N-(2-(N-methylnonafluorobutanesulfonamido)ethyl)propionamide. This amide was twice extracted with 250 mL deionized water, heated for 18 hours at 100° C. with a mixture of 250 mL concentrated hydrochloric acid and 100 mL deionized water, extracted with 925 mL of 24 weight percent aqueous sodium hydroxide solution, extracted with 250 mL 10 weight percent aqueous sodium hydroxide solution, and distilled to provide N-(2-aminoethyl)-N-methylnonafluorobutanesulfonamide (538 g; 75 percent recovery; 94 percent pure by gas chromatography (GC); distilled at 104-109° C. under 2 mm Hg pressure).
Sources & evidence
- ORD record
- ord-d1cfb31d96d4480491bfcdaa5a57b11b
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08858813B2
Linked notes
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