Phenyl isocyanate → HCID 53903353, compound

HRID 1708115Notes

Reaction equation

HRID 1708115 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][N:9]([OH:13])[CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][N:9]([O:13][C:21]([NH:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:22])[CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 54140687HCID 54140687, compound

Product 1

HCID 53903353HCID 53903353, compoundYield 33%

Procedure

α-(Methoxyimino)-α-(1-hydroxy-1,2,5,6-tetrahydropyridin-3-yl)acetonitrile (E2) (0.45 g, 0.0025 moles) was treated with phenyl isocyanate as in the method of Example 8. The residue obtained was chromatographed on silica gel eluting with 0-1% methanol/chloroform to give a crystalline solid. Recrystallisation from ethyl acetate/60-80 petrol gave the title compound (E9) as white crystals (0.245 g, 33%) m.p. 128°-130° C.

Workup

  1. customThe residue obtained
  2. customwas chromatographed on silica gel eluting with 0-1% methanol/chloroform
  3. customto give a crystalline solid
  4. customRecrystallisation from ethyl acetate/60-80 petrol

Sources & evidence

ORD record
ord-f6e59e1945894b76839a58d557e6adda
Source dataset
uspto-grants-1994_10
Patent number
US05356914

Reaction notes

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