Phenyl isocyanate → Formamide, N-1-naphthalenyl-

HRID 1703982Notes

Reaction equation

HRID 1703982 reaction equation
C1(N=C=O)C=CC=CC=1.[C:10]1([N:20]=[C:21]=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>>[C:10]1([NH:20][CH:21]=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 66589alpha-Naphthyl isocyanate

Product 1

HCID 96004Formamide, N-1-naphthalenyl-Yield 94%

Procedure

The catalytic hydrogenation procedure of Example 1 was repeated except that the phenyl isocyanate used therein was replaced by 1.7 g. (0.01 mole) of 1-naphthylisocyanate. Reduction was complete in 45 minutes. The catalyst was removed by filtration and the colorless filtrate then evaporated to dryness giving 1.71 g. of tan-white crude product, m.p. 134° - 135° C. The solid was recrystallized from ethanol-water to give 1.62 g. (94% yield) of dried title product, m.p. 137.5° - 138.5° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe colorless filtrate then evaporated to dryness
  3. customgiving 1.71 g
  4. customThe solid was recrystallized from ethanol-water
  5. customto give 1.62 g
  6. dry with material(94% yield) of dried title product, m.p. 137.5° - 138.5° C.

Sources & evidence

ORD record
ord-8825c44c40eb4b4e97de72d748172e3a
Source dataset
uspto-grants-1978_11
Patent number
US04125724

Reaction notes

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