(Pentafluorophenyl)hydrazine → ethyl N-trifluoroacetyl-N-(bis(pentafluorophenylhydrazino)phosphonomethyl)glycinate
Reaction equation
[F:1][C:2]1[C:7]([NH:8][NH2:9])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].[F:14][C:15]([F:33])([F:32])[C:16]([N:18]([CH2:25][P:26]([O:30]Cl)([O:28]Cl)=[O:27])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17]>O1CCCC1>[F:14][C:15]([F:33])([F:32])[C:16]([N:18]([CH2:25][P:26]([O:30][NH:9][NH:8][C:7]1[C:6]([F:10])=[C:5]([F:11])[C:4]([F:12])=[C:3]([F:13])[C:2]=1[F:1])([O:28][NH:9][NH:8][C:7]1[C:2]([F:1])=[C:3]([F:13])[C:4]([F:12])=[C:5]([F:11])[C:6]=1[F:10])=[O:27])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17]Participants
4
Procedure
To a solution of pentafluorophenylhydrazine (3.96 g, 0.02 mole) in 40 ml. of tetrahydrofuran at 0° C. was added over 1/2 hour ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (1.65 g, 0.005 mole) in 40 ml. of tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and stir for 2 hours, then filtered. The filtrate was washed with water, dried, and concentrated in vacuo to yield a dark red-brown solid. This solid was washed several times with 70% ether in petroleum ether to yield ethyl N-trifluoroacetyl-N-(bis(pentafluorophenylhydrazino)phosphonomethyl)glycinate, m.p. 100°-110° C.
Workup
- filtrationfiltered
- washThe filtrate was washed with water
- customdried
- concentrationconcentrated in vacuo
- customto yield a dark red-brown solid
- washThis solid was washed several times with 70% ether in petroleum ether
Sources & evidence
- ORD record
- ord-1b30cea2ece54cb2b35a3d244607a232
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04359332
Reaction notes
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