Hydrochloric Acid → HCID 178484893, compound

HRID 1658672Notes

Reaction equation

HRID 1658672 reaction equation
[B-](F)(F)(F)F.CC[O+](CC)CC.[CH3:13][NH:14][C:15](=O)[C:16]([O:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17].[B-](F)(F)(F)F.[Br:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=1[C:37]([F:40])([F:39])[F:38].Cl>C(O)C.C(Cl)Cl>[CH3:13][NH:14][C:15](=[N:34][C:33]1[CH:35]=[CH:36][C:30]([Br:29])=[C:31]([C:37]([F:40])([F:38])[F:39])[CH:32]=1)[C:16]([O:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 26255Tetrafluoroborate2×HCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 2723982Triethyloxonium tetrafluoroborateHCID 215281362-Methyl-1-(methylamino)-1-oxopropan-2-yl acetate

Product 1

HCID 178484893HCID 178484893, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Over a five minute period, add a solution of 17.5 g. (0.10 moles) of triethyloxonium fluoborate in 50 ml. of methylene chloride to a mixture of 15.9 g. (0.10 moles) of N-methyl-2-acetoxyisobutyramide in 200 ml. of dry methylene chloride at 0°-5°C. Allow to warm to room temperature and stir for sixteen hours. Remove the solvent in vacuo and obtain the crude product of this reaction as its fluoborate salt. Dissolve the crude fluoborate salt in 150 ml. of anhydrous ethanol, add 24.0 g. (0.10 moles) of 4-bromo-3-trifluoromethylaniline and stir for three days. Remove the solvent in vacuo and partition the residue between ether and saturated aqueous sodium bicarbonate solution. Retain the ether solution, dry it over sodium sulfate and precipitate the product of this reaction as its hydrochloride salt, by adding 0.10 moles of ethereal hydrogen chloride (25 ml. of a 4.0N solution).

Workup

  1. additionadd a solution of 17.5 g
  2. customat 0°-5°C
  3. customRemove the solvent in vacuo
  4. customobtain
  5. customRemove the solvent in vacuo
  6. custompartition the residue between ether and saturated aqueous sodium bicarbonate solution
  7. dry with materialRetain the ether solution, dry it over sodium sulfate
  8. customprecipitate
  9. customthe product of this reaction as its hydrochloride salt

Sources & evidence

ORD record
ord-14641d6bb7324540a44d3318349b9739
Source dataset
uspto-grants-1976_06
Patent number
US03965176

Reaction notes

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