Toluene → HCID 15230862, compound

HRID 1464499Notes

Reaction equation

HRID 1464499 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[C:14](=[O:15])[C:13]([CH3:16])=[C:12]([CH3:17])[C:11](=[O:18])[C:10]=1[CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].[O-:32][C:33]#[N:34].[K+].FC(F)(F)C(O)=O>O>[C:33](=[O:32])([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]([C:10]1[C:11](=[O:18])[C:12]([CH3:17])=[C:13]([CH3:16])[C:14](=[O:15])[C:9]=1[CH3:8])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:34]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 11378442Potassium cyanateHCID 19088049HCID 19088049, compound

Product 1

HCID 15230862HCID 15230862, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (10 ml) was added to 1.20 g (3.68 mmole) of 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-phenylhexanol and 0.90 g (3.68×3 mmole) of potassium cyanate, followed by stirring at room temperature, and 1.38 g (3.68×3.3 mmole) of trifluoroacetic acid was added to the mixture over the 5-minutes period. 5 Minutes later, the reaction temperature was raised to 40° C., and stirring was effected at 35° to 40° C. for 3 hours. After water was added, the insoluble matter was filtered out, and isopropyl ether was added to the filtrate to effect extraction. The organic layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residue was chromatographed on a silica gel column to elute with isopropyl ether to give 0.79 g (58%, recrystallized from isopropyl ether) of 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-phenylhexyl carbamate. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound No. 59 was prepared.

Workup

  1. temperature5 Minutes later, the reaction temperature was raised to 40° C.
  2. stirringstirring
  3. filtrationthe insoluble matter was filtered out
  4. additionisopropyl ether was added to the filtrate
  5. extractionextraction
  6. customThe organic layer was separated out
  7. washwashed with aqueous sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated
  10. customThe residue was chromatographed on a silica gel column
  11. washto elute with isopropyl ether

Sources & evidence

ORD record
ord-dc01b87787e04c19a7929cb35127f667
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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