2-Methylphenyl isothiocyanate → HCID 18188094, compound

HRID 49706Notes

Reaction equation

HRID 49706 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[CH:4][C:3]=1[OH:17].[C:18]1([CH3:27])[C:19]([N:24]=[C:25]=S)=[CH:20][CH:21]=[CH:22][CH:23]=1>C(O)C>[CH3:8][C:7]1[C:2]2[N:1]=[C:25]([NH:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:27])[O:17][C:3]=2[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=1

Participants

4

Reactant 2

HCID 691952-Methylphenyl isothiocyanateHCID 18188095t-Butyl 4-amino-3-hydroxy-5-methyl-phenylacetate

Product 1

HCID 18188094HCID 18188094, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of t-butyl 4-amino-3-hydroxy-5-methyl-phenylacetate (0.38 g, Reference Example 10) in ethanol (10 mL) and o-tolylisothiocyanate (0.24 g) was stirred for 7 hours, then left to stand over night and then evaporated. The residue was dissolved in ethanol (10 mL) and the solution was treated with dicyclohexylcarbodiimide (0.36 g). This mixture was heated at reflux temperature for 2 hours and then evaporated. The residual gum was dissolved in dichloromethane (15 mL) and the solution was treated with trifluoroacetic acid (4.75 mL). After standing at room temperature for 3 hours the mixture was evaporated and the residue was dissolved in diethyl ether. This solution was extracted twice with saturated sodium bicarbonate solution and the pH of the combined aqueous extracts was adjusted to 1-2 by addition of dilute hydrochloric acid. This solution was then extracted with ethyl acetate and the extract was washed with brine, then dried and then evaporated to give the title compound (0.33 g) as a pale yellow solid.

Workup

  1. waitleft
  2. waitto stand over night
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethanol (10 mL)
  5. additionthe solution was treated with dicyclohexylcarbodiimide (0.36 g)
  6. temperatureThis mixture was heated
  7. temperatureat reflux temperature for 2 hours
  8. customevaporated
  9. dissolutionThe residual gum was dissolved in dichloromethane (15 mL)
  10. additionthe solution was treated with trifluoroacetic acid (4.75 mL)
  11. waitAfter standing at room temperature for 3 hours
  12. customthe mixture was evaporated
  13. dissolutionthe residue was dissolved in diethyl ether
  14. extractionThis solution was extracted twice with saturated sodium bicarbonate solution
  15. additionthe pH of the combined aqueous extracts was adjusted to 1-2 by addition of dilute hydrochloric acid
  16. extractionThis solution was then extracted with ethyl acetate
  17. washthe extract was washed with brine
  18. customdried
  19. customevaporated

Sources & evidence

ORD record
ord-c38f0cc24a4e4187a72395a6890f0e0d
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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