Water → HCID 19373551, compound

HRID 129107Notes

Reaction equation

HRID 129107 reaction equation
[C:1]([CH2:3][C:4](OC)(OC)[O:5][CH3:6])#[N:2].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[CH3:6][O:5][C:4](=[N:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 1443813,3,3-Trimethoxypropionitrile

Product 1

HCID 19373551HCID 19373551, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolvent2×

Procedure

In a 250-mL flask was placed 87 g (0.6 mol) of 2-cyano-1,1,1-trimethoxyethane, 46.5 g (0.5 mol) of aniline, and 1.0 g (0.005 mol) of p-toluenesulfonic acid monohydrate. The mixture was placed in a pre-heated oil bath at 120° C. and stirred rapidly. The methanol by-product of the reaction was allowed to boil off. When the internal reaction temperature reached 110° C., the reaction flask was fitted with a water aspirator vacuum take-off, and the residual methanol was removed at approximately 20 mm Hg. The crude product mixture was then distilled under high vacuum and the fraction distilling at 115°-125° C. (0.5 mm Hg) was collected to give 47.6 g (0.27 mol, 54.6% yield) of methyl-2-cyano-N-phenylacetimidate as a light yellow liquid, which was characterized by NMR and mass spectral data. HPLC analysis showed this material to be 96% pure. Elemental analysis: Calculated: C, 68.95; H, 5.79; N, 16.08. Found: C, 66.80, H, 5.72, N, 15.36.

Workup

  1. customIn a 250-mL flask was placed
  2. customThe mixture was placed in a pre-heated oil bath at 120° C.
  3. customreached 110° C.
  4. customwas removed at approximately 20 mm Hg
  5. distillationThe crude product mixture was then distilled under high vacuum
  6. distillationthe fraction distilling at 115°-125° C. (0.5 mm Hg)
  7. customwas collected

Sources & evidence

ORD record
ord-79a859ea0eaf470886605c0e74b02488
Source dataset
uspto-grants-1995_11
Patent number
US05466813

Reaction notes

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