2,4,6-Trichloroaniline → HCID 54270300, compound

HRID 648275Notes

Reaction equation

HRID 648275 reaction equation
O=[C:2]([CH:20]([CH3:22])[CH3:21])[C:3]([O:5]CC1C=CC=C(OC2C=CC=CC=2)C=1)=[O:4].[Cl:23][C:24]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[C:25]=1[NH2:26]>C1C=CC=CC=1>[Cl:23][C:24]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[C:25]=1[NH:26][C@H:2]([C:3]([OH:5])=[O:4])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 124712,4,6-TrichloroanilineHCID 20482721HCID 20482721, compound

Product 1

HCID 54270300HCID 54270300, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.5 g of m-phenoxybenzyl 2-oxo-3-methylbutanoate, 0.39 g of 2,4,6-trichloroaniline, 0.02 g of p-toluenesulfanylacetate and 10 ml of benzene is heated to reflux for about 5.5 hr. A Dean-Stark trap is used to remove water. The reaction is worked by pouring into ether/sodium bicarbonate solution. The organic phase is washed with water and brine, dried over magnesium sulfate and evaporated. To the reaction product (0.79 g) is added 3 ml of methanol, 1 ml of THF and 0.19 g of NaCNBH3. The reaction mixture is stirred at RT and then adjusted to pH 3 to 4 with concentrated sulfuric acid. Stirring at RT is continued overnight. The reaction is worked up as before using ether/sodium bicarbonate solution and subjected to prep. TLC eluting with 20% ether/hexane to yield the m-phenoxybenzyl ester of N-(2,4,6-trichlorophenyl)valine, MS m/e 477 (M+).

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 5.5 hr
  3. customto remove water
  4. additionby pouring into ether/sodium bicarbonate solution
  5. washThe organic phase is washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionTo the reaction product (0.79 g) is added 3 ml of methanol, 1 ml of THF and 0.19 g of NaCNBH3
  9. stirringStirring at RT
  10. washTLC eluting with 20% ether/hexane

Sources & evidence

ORD record
ord-7316f39014ed4949ac56d469a7d1cc41
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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