Cyclohexylamine → HCID 53814580, compound

HRID 223304Notes

Reaction equation

HRID 223304 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:8][C:9]([F:27])([F:26])[C:10]([N:12]([CH2:19][P:20]([O:24]Cl)([O:22]Cl)=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]>CCOCC>[F:8][C:9]([F:27])([F:26])[C:10]([N:12]([CH2:19][P:20]([O:24][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O:22][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 53814580HCID 53814580, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of cyclohexylamine (14.6 g, 0.147 mole) in 100 ml. of ether was added dropwise with stirring ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (11.55 g, 0.035 mole) in 200 ml. of ether. The reaction was stirred overnight at room temperature, then filtered and the filtrate concentrated in vacuo to yield a gum-solid. Upon trituration with petroleum ether, ethyl N-trifluoroacetyl-N-(bis(cyclohexylamino)phosphonomethyl)glycinate (6.65 g) was obtained as a white solid, m.p. 118.5°-123° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto yield a gum-solid

Sources & evidence

ORD record
ord-87e96a2a87b74b2d9326fd29935f8c24
Source dataset
uspto-grants-1982_10
Patent number
US04353731

Reaction notes

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