Di-tert-butyl peroxide → HCID 20566760, compound
Reaction equation
[CH2:1]([N:4]([CH2:12][CH2:13][CH2:14][CH3:15])[S:5]([C:8]([F:11])([F:10])[F:9])(=[O:7])=[O:6])[CH:2]=[CH2:3].C(OOC(C)(C)C)(C)(C)C.[CH2:26]([O:28][P:29]([O-:33])[O:30][CH2:31][CH3:32])[CH3:27]>>[CH2:12]([N:4]([CH2:1][CH2:2][CH2:3][P:29]([O:30][CH2:31][CH3:32])(=[O:33])[O:28][CH2:26][CH3:27])[S:5]([C:8]([F:11])([F:9])[F:10])(=[O:7])=[O:6])[CH2:13][CH2:14][CH3:15]Participants
Conditions
- Temperature
- 150 °C
Procedure
Over a 60 minute period, a solution of the above-prepared N-allylsulfonamide (24.60 g, 0.10 mole) and diethylphosphite (15 g) was added dropwise concurrently with a solution of di-t-butyl peroxide (0.90 g) in diethylphosphite (5 g) to diethylphosphite (80 g) being stirred at 150° C. with an argon purge. The resulting mixture was stirred for an additional 1 hour under these conditions. The excess diethylphosphite was distilled at 10-20 torr and the residue fractionally distilled to give 19.64 g (b.p. 150°-153° C. at 0.20 torr) of the desired compound, diethyl 3-(N-butyltrifluoromethanesulfonamido)propanephosphonate. A mixture of the phosphonate prepared above (15.36 g, 0.040 mole) and bromotrimethylsilane (13.46 g. 0.088 mole) was stirred under a reflux condensor and calcium chloride drying tube for 96 hours. Then water (75 ml) was added and the resulting mixture stirred for 15 minutes followed by extraction with three 50 ml portions of diethylether. The ether portions were combined, dried with MgSO4 and evaporated in vacuo to give 12.25 g of the desired compound, 3-(N-butyltrifluoromethanesulfonamido)propanephosphonic acid.
Workup
- custompurge
- stirringThe resulting mixture was stirred for an additional 1 hour under these conditions
- distillationThe excess diethylphosphite was distilled at 10-20 torr
- distillationthe residue fractionally distilled
Sources & evidence
- ORD record
- ord-c657fd1e61b54772b577205b6c852cef
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04293441
Reaction notes
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