Diethylphosphite → HCID 20566761, compound
Reaction equation
C(NS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)C.[CH2:20]([N:23]([CH2:40][CH3:41])[S:24]([C:27]([F:39])([F:38])[C:28]([F:37])([F:36])[C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])(=[O:26])=[O:25])[CH:21]=[CH2:22].[CH2:42]([O:44][P:45]([O-:49])[O:46][CH2:47][CH3:48])[CH3:43]>>[CH2:40]([N:23]([CH2:20][CH2:21][CH2:22][P:45]([O:46][CH2:47][CH3:48])(=[O:49])[O:44][CH2:42][CH3:43])[S:24]([C:27]([F:39])([F:38])[C:28]([F:36])([F:37])[C:29]([F:34])([F:35])[C:30]([F:31])([F:32])[F:33])(=[O:26])=[O:25])[CH3:41]Participants
Procedure
The procedure of Example 1 was repeated with the exception that N-ethylperfluorobutanesulfonamide was used in place of N-butyltrifluoromethanesulfonamide to make N-allyl-N-ethylperfluorobutanesulfonamide (b.p. 50°-55° C. at 0.12 to 0.10 torr). The latter was reacted with diethylphosphite to produce the desired compound, diethyl 3-(N-ethylperfluorobutanesulfonamido)propanephosphonate (b.p. 148°-152° C. at 0.4-0.5 torr). A solution of the phosphonate prepared in Example 3 (30.0 g, 0.062 mole) and bromotrimethylsilane (20.0 g, 0.130 mole) was stirred under a reflux condenser and calcium chloride drying tube for 24 hours, water (75 ml) was added, and the mixture stirred for 15 minutes. The resulting white precipitate was filtered and washed with water (50 ml) and diethylether (100 ml), then dried in an oven at 100° C. for 24 hours at 10-20 torr, to yield the desired compound, 3-(N-ethylperfluorobutanesulfonamido)propanephosphonic acid (m.p. 138.5°-140° C.).
Sources & evidence
- ORD record
- ord-dc9393a675c94b19ae8da7e968601f5f
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04293441
Reaction notes
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