Diethyl Ether → HCID 178456612, compound

HRID 1906369Notes

Reaction equation

HRID 1906369 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12]([N:15]=[C:16]=[S:17])[CH:13]=[CH2:14].CCOCC>C(Cl)Cl>[CH2:12]([N:15]1[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=[C:16]1[SH:17])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5971Allyl IsothiocyanateHCID 8635Methyl Anthranilate

Product 1

HCID 178456612HCID 178456612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
40 °C

Procedure

To a stirred mixture of 50 g (0.33 mole) methyl anthranilate in 100 ml methylene chloride, 32.7 g (0.33 mole) allyl isothiocyanate in 50 ml methylene chloride was added dropwise. The reaction mixture was refluxed at 40° C. one hour, stirred over the weekend at ambient temperature, and refluxed at 40° C. for one hour. The reaction mixture was stripped. Additional methylene chloride (200 ml) was added; the resulting mixture was refluxed at 40° C. for 7 hours, and then stirred about 11/2 days at ambient temperature. The reaction mixture was stripped. Ether was added; a precipitate formed. The above-identified product was isolated by suction filtration.

Workup

  1. additionwas added dropwise
  2. temperaturerefluxed at 40° C. for one hour
  3. temperaturethe resulting mixture was refluxed at 40° C. for 7 hours
  4. stirringstirred about 11/2 days at ambient temperature
  5. customa precipitate formed
  6. customThe above-identified product was isolated by suction filtration

Sources & evidence

ORD record
ord-f93c5230d81d4a88b73e37aa10963d62
Source dataset
uspto-grants-1987_03
Patent number
US04652558

Reaction notes

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