Methanol → HCID 86755349, compound
Reaction equation
[F:1][C:2]([F:19])([C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:4][C:5](OC)=O.[F:20][C:21]([F:36])([C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])[CH2:22][CH2:23][CH2:24][NH2:25].C[OH:38]>>[F:1][C:2]([F:19])([C:9]([F:17])([F:18])[C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[CH2:3][CH2:4][CH2:5][CH:23]([CH2:22][C:21]([F:36])([F:20])[C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:29])([F:30])[F:31])[C:24]([NH2:25])=[O:38]Participants
Procedure
A mixture of methyl 4,4,5,5,6,6,7,7,7-nonafluoroheptanoate (18 g 59 mmol) and 4,4,5,5,6,6,7,7,7-nonafluoroheptylamine (18.5 g, 66.8 mmol) was heated to slowly distill MeOH out through a 15 cm long column. Colorless liquid (10.5 g) was obtained by atmospheric and then full vacuum distillation. After being cooled to RT, the residue in the reaction flask was solidified to a yellow solid (26.0 g). NMR and GC-MS analysis indicated that it was the product, N-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-4,4,5,5,6,6,7,7,7-nonafluoroheptanamide, 80% yield. 19F NMR (CDCl3) -81.6 (t, J=10Hz, 6F), -115.0 (m, 2F), -115.4 (m, 2F), -125.0 (m, 4F), -126.6 (m, 4F) ppm. 1H NMR (CDCl3) 1.85 (m, 2H), 2.12 (m, 2H), 2.42-2.61 (m, 4H), 3.38 (q, J=7 Hz, 2H), 5.70 (br s, 1H) ppm. 13C NMR (CDCl3) 21.0 (s), 26.9 (t, J=23 Hz), 27.3 (s), 28.5 (t, J=23 Hz), 39.0 (s), 170.0 (s), 115-122 (m) ppm. MS (m/e) 532 (M+ -F, 37.5%), 482 (M+ -CF3, 0.3%), 382 (M+ -C3F7, 20.5%), 332 (M+ -C3F7, 58.7%), 275 (88.1%), 169 (1.8%), 119 (26.7%), 69 (100%).
Sources & evidence
- ORD record
- ord-5c78c0130ddd44f5a7d525a32f7f8f13
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054615
Reaction notes
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