Exalamide → HCID 12254260, compound

HRID 1288263Notes

Reaction equation

HRID 1288263 reaction equation
[CH2:1]([O:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[B-](F)(F)(F)F.[CH3:22][CH2:23][O+](CC)CC>C(Cl)Cl>[CH2:1]([O:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](=[NH:12])[O:11][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3316ExalamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 12254260HCID 12254260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-hexyloxybenzamide (64 g; prepared as described by E. M. Bavin, F. J. Macrae, D. E. Seymour and P. D. Waterhouse, J.Pharm.Pharmacol., 1952, 4, 872) in anhydrous methylene chloride (830 ml.) was added, dropwise during 10 minutes with stirring, a solution of triethyloxonium borofluoride (55.2 g.) in anhydrous methylene chloride (170 ml.). The solution was stirred for a further 105 minutes, and allowed to stand at room temperature for 2 days. The solution was concentrated to 350 ml., and anhydrous diethyl ether (1750 ml.) was added. The precipitated solid was filtered off and washed with anhydrous diethyl ether to give ethyl 2-hexyloxybenzimidate borofluoride (62 g.), m.p. 68°-70° C., which was pure enough to use for the next stage of the synthesis. A pure sample, m.p. 73°-74° C., was obtained by recrystallisation of an aliquot from a mixture of anhydrous methylene chloride and anhydrous diethyl ether.

Workup

  1. stirringThe solution was stirred for a further 105 minutes
  2. concentrationThe solution was concentrated to 350 ml
  3. addition, and anhydrous diethyl ether (1750 ml.) was added
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with anhydrous diethyl ether

Sources & evidence

ORD record
ord-cd77abc13c7a4f1e8d4f435e89bdf3d7
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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