Water → HCID 19002023, compound

HRID 2259960Notes

Reaction equation

HRID 2259960 reaction equation
CNN.[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:12](=[O:25])[CH2:13][N:14]1[C:18](=[O:19])C2=CC=CC=C2C1=O.O.[CH3:35][C:36]1[CH:37]=[C:38]([N:42]=C=O)[CH:39]=[CH:40][CH:41]=1>ClCCl.O1CCCC1>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH2:26][C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[C:12](=[O:25])[CH2:13][NH:14][C:18]([NH:42][C:38]1[CH:39]=[CH:40][CH:41]=[C:36]([CH3:35])[CH:37]=1)=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6061MethylhydrazineHCID 69303m-Tolyl isocyanateHCID 19001995HCID 19001995, compound

Product 1

HCID 19002023HCID 19002023, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Methyl hydrazine (2.13 g) is added at a temperature in the region of 0° C. to a solution of tert-butyl 2-[N-(2-methylphenyl)-2-phthalimidoacetamido]acetate (5.5 g) in dichloromethane (90 cc). The reaction mixture is stirred for 30 hours at a temperature in the region of 20° C. and then for 1 hour under reflux. After cooling, water (100 cc) is added, the mixture is stirred and the aqueous phase is separated after settling has taken place and re-extracted with dichloromethane (2×60 cc). The organic phases are combined, washed with water (2×15 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. tert-Butyl 2-[2-amino-N-(2-methylphenyl)acetamido]acetate is thereby obtained in the form of an oil, which is dissolved in anhydrous tetrahydrofuran (40 cc). 3-Methylphenyl isocyanate (1.77 g) is added to this solution and the reaction mixture is then stirred for 1 hour at a temperature in the region of 20° C. and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation in petroleum ether, tert-butyl 2-{N-(2-methylphenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (1.05 g), m.p. 133° C., is obtained.

Workup

  1. temperaturefor 1 hour under reflux
  2. temperatureAfter cooling
  3. stirringthe mixture is stirred
  4. customthe aqueous phase is separated after settling
  5. extractionre-extracted with dichloromethane (2×60 cc)
  6. washwashed with water (2×15 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C. tert-Butyl 2-[2-amino-N-(2-methylphenyl)acetamido]acetate
  10. customis thereby obtained in the form of an oil, which
  11. stirringthe reaction mixture is then stirred for 1 hour at a temperature in the region of 20° C.
  12. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  13. customAfter recrystallisation in petroleum ether

Sources & evidence

ORD record
ord-03440eebb3b4487cbced43b8195557d2
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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