Phenyl isocyanate → HCID 18967544, compound

HRID 235122Notes

Reaction equation

HRID 235122 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[C:19]1([NH:25][C:26]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanate2×HCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 18967544HCID 18967544, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.216 g, 0.896 mmol) and phenyl isocyanate (0.222 g, 1.86 mmol) were combined in acetonitrile (14 mL) and refluxed overnight. Phenyl isocyanate (0.106 g, 0.896 mmol) was added and the reaction was refluxed 2 hours more. Upon cooling a tan solid precipitated which was collected and recrystallized from methanol/ethyl acetate to give 0.202 g (62%) of the title product; mp 213°-214° C. Analysis calculated for C22H24N4O: C, 73.31; H, 6.71; N, 15.54. Found: C0 73.03; H, 6.55; N, 15.22.

Workup

  1. temperaturerefluxed overnight
  2. temperaturethe reaction was refluxed 2 hours more
  3. temperatureUpon cooling a tan solid
  4. customprecipitated which
  5. customwas collected
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-3657ca6388ac45dd948128ce5a8e346d
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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