m-Tolyl isocyanate → HCID 19001957, compound

HRID 2259944Notes

Reaction equation

HRID 2259944 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]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)=[O:14]>O1CCCC1>[Cl:22][C:18]1[CH:17]=[C:16]([N:15]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13](=[O:14])[CH2:12][NH:11][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:10])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19001963HCID 19001963, compound

Product 1

HCID 19001957HCID 19001957, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

3-Methylphenyl isocyanate (0.6 g) is added at a temperature in the region of 20° C. to a solution of tert-butyl 2-[2-amino-N-(3-chlorophenyl)acetamido]-acetate (1.25 g) in anhydrous tetrahydrofuran (20 cc). The solution obtained is stirred for 4 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: ethyl cyclohexaneacetane [sic] (75:25 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 crystallisation in diisopropyl ether, tert-butyl 2-{N-(3-chlorophenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (0.8 g), m.p. 110° 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 crystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-9532d6e6b7e541c685cd1dbdc76e620a
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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