Phenol → HCID 54239202, compound

HRID 1448424Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:15][C:16]([F:34])([F:33])[C:17]([N:19]([CH2:26][P:27]([O:31]Cl)([O:29]Cl)=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18].[NH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>CCOCC>[F:15][C:16]([F:34])([F:33])[C:17]([N:19]([CH:26]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[P:27]([OH:31])([O:29][NH:35][N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of phenol (2.3 g, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (8.25 g, 0.025 mole) in 150 ml. of ether at 0° C. After two hours, the solution was filtered and the filtrate was added to a cooled (0° C.) solution of N-aminopiperidine (5.2 ml, 0.05 mole) in 100 ml. of ether. The resulting solution was stirred at 25° C. for 16 hours, then filtered. The filtrate was washed with 0.3% hydrochloric acid, dried over sodium sulfate and concentrated in vacuo to afford ethyl N-trifluoroacetyl-N-(phenoxy(N-piperidinoamino)phosphonomethyl)glycinate which could not be further purified by any means.

Workup

customat 0° C
filtrationthe solution was filtered
additionthe filtrate was added to
filtrationfiltered
washThe filtrate was washed with 0.3% hydrochloric acid
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-55f22857c9f74aac86c01663204a3edd
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

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