Ethyl isocyanate → HCID 135948879, compound

HRID 1034954Notes

Reaction equation

HRID 1034954 reaction equation
[C:1]1([C:7]2[C:11]([CH3:12])=[N:10][N:9]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:8]=2[NH2:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(N=[C:22]=[O:23])C.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][N:9]1[C:8]2[NH:18][C:22](=[O:23])[C:2]3[CH2:3][CH2:4][CH2:5][CH2:6][C:1]=3[C:7]=2[C:11]([CH3:12])=[N:10]1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8857Ethyl AcetateHCID 69475776HCID 69475776, compound

Product 1

HCID 135948879HCID 135948879, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of EXAMPLE 8A (1.05 g, 4.22 mmol) in pyridine (10 mL) was added ethyl isocyanate (1.0 mL, 12.68 mmol) and the solution heated at reflux overnight. The mixture was cooled, stirred with 15 mL ethyl acetate at ambient temperature for 5 minutes and the solid collected by filtration, washed with ethyl acetate and dried to give 793 mg of the title compound. The mother liquor was concentrated and the residue recrystallized from ethyl acetate to give an additional 300 mg of the title compound (94% overall yield). 1H NMR (DMSO-d6) 1.64-1.75 (m, 4H), 2.16 (s, 6H), 2.34-2.39 (m, 5H), 2.59 (t, J=6.4 Hz, 2H), 2.83-2.87 (m, 2H), 4.18 (t, J=6.6 Hz, 2H).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe solid collected by filtration
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-52dd2ac03402428f987e948c9a7444bb
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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