m-Tolyl isocyanate → HCID 15670989, compound

HRID 2259966Notes

Reaction equation

HRID 2259966 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:11][CH2:12][C:13]([N:15]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14]>O1CCCC1>[NH:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:15]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:13](=[O:14])[CH2:12][NH:11][C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:10])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19002014HCID 19002014, compound

Product 1

HCID 15670989HCID 15670989, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

3-Methylphenyl isocyanate (1.07 g) is added at a temperature in the region of 20° C. to a solution of tert-butyl 2-[2-amino-N-(2-anilinophenyl)acetamido]acetate (2.6 g) in anhydrous tetrahydrofuran (20 cc). The solution obtained is stirred for 2 hours at a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residual oil is purified by chromatography on silica (0.063-0.2 mm) (150 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate (50:50 by volume)], collecting 20-cc fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation in ethyl acetate, tert-butyl 2-{N-(2-anilinophenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (1.15 g), m.p. 180° C., is obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  3. customThe residual oil is purified by chromatography on silica (0.063-0.2 mm) (150 g)
  4. customcollecting 20-cc fractions
  5. additionThe fractions containing only the desired product
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallisation in ethyl acetate

Sources & evidence

ORD record
ord-2c9e22fd13a34b9dae86b078ba521d65
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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