m-Tolyl isocyanate → HCID 15670970, compound

HRID 1769722Notes

Reaction equation

HRID 1769722 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13](=[O:24])[N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>>[CH3:25][C:26]1[CH:27]=[C:28]([NH:32][C:33](=[O:34])[NH:1][CH2:2][C:3]([N:5]([CH2:12][C:13](=[O:24])[N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:4])[CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 20097112HCID 20097112, compound

Product 1

HCID 15670970HCID 15670970, compoundYield 36.5%

Procedure

The procedure is analogous to that described in Example 106, but 2.0 g of 2-amino-N-[2-oxo-2-(1,2,3,4-tetrahydro-2-isoquinolyl)ethyl]-N-phenylacetamide and 0.8 g of 3-methylphenyl isocyanate are used as the starting material. The crude product is purified by chromatography on 70 g of silica (0.065-0.200 mm) contained in a column 2.5 cm in diameter [eluent: methylene chloride/methanol (98-2 by volume)], collecting 20 cm3 fractions. Fractions 12 to 26 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from ethyl acetate, 1.0 g of 2-[3-(3-methylphenyl)ureido]-N-[2-oxo-2-(1,2,3,4-tetrahydro-2-isoquinolyl)ethyl]-N-phenylacetamide melting at 135° C is obtained.

Workup

  1. customThe crude product is purified by chromatography on 70 g of silica (0.065-0.200 mm)
  2. customcollecting 20 cm3 fractions
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  4. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3eb0813e07ff4b1c99cbf220dbfbec1f
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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