m-Tolyl isocyanate → HCID 19002028, compound

HRID 2259954Notes

Reaction equation

HRID 2259954 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]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)=[O:14]>O1CCCC1>[CH3:23][N:22]([CH3:24])[C:19]1[CH:18]=[CH:17][C:16]([N:15]([CH2:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[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]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19002012HCID 19002012, compound

Product 1

HCID 19002028HCID 19002028, compoundYield 697.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

3-Methylphenyl isocyanate (0.35 g) is added at a temperature in the region of 20° C. to a solution of tert-butyl 2-[2-amino-N-(4-dimethylaminophenyl)acetamido]acetate (0.7 g) in anhydrous tetrahydrofuran (15 cc). The solution obtained is stirred for 3 hours at a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation of the residual solid in ethyl acetate, tert-butyl 2-{N-(4-dimethylaminophenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (0 7 g), m.p 105° C., is obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  3. customAfter recrystallisation of the residual solid in ethyl acetate

Sources & evidence

ORD record
ord-2eea7f03be98424484159ac4153249c5
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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