Trifluoroacetic anhydride → 2-Phenoxy-alpha-methoxyiminobenzyl cyanide

HRID 6363

Reaction equation

HRID 6363 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[N:18][O:19][CH3:20])[C:15]([NH2:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1.Cl>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[N:18][O:19][CH3:20])[C:15]#[N:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 539671372-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

Product 1

HCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanideYield 96.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Phenoxyphenyl)-2-methoxyiminoacetamide (3.77 g) was dissolved in pyridine (5.53 g). The solution was cooled to 0° C. Trifluoroacetic anhydride (4.40 g) was added dropwise. The mixture was stirred for 2 hours at 0° C., and then diluted with dil. hydrochloric acid and extracted with ethyl acetate. The extract was dried and concentrated to leave a residue, which was purified by column chromatography on silica gel to obtain 2-(2-phenoxyphenyl)-2-methoxyiminoacetonitrile (3.41 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated
  4. customto leave a residue, which
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8551d82337ad4e2ca282f87e462a018c
Source dataset
uspto-grants-1993_09
Patent number
US05248687

Linked notes

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