Dimethylformamide dimethyl acetal → N'-(2-Cyano-3,6-difluorophenyl)-N,N-dimethylformamidine

HRID 1467398Notes

Reaction equation

HRID 1467398 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[C:4]([C:3]1[C:6]([F:11])=[CH:7][CH:8]=[C:9]([F:10])[C:2]=1[N:1]=[CH:14][N:15]([CH3:17])[CH3:16])#[N:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 450905912-Amino-3,6-difluorobenzonitrile

Product 1

HCID 59223042N'-(2-Cyano-3,6-difluorophenyl)-N,N-dimethylformamidineYield 797.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-amino-3,6-difluorobenzonitrile (1.92 g, 12.5 mmol) and N,N-dimethylformamide dimethyl acetal (2.2 mL, 1.3 mmol) in 15 mL of toluene was heated to reflux for 1 h. The reaction was complete based on GC-MS. The solvent was removed in vacuo and the oily residue was suspended in hexane and a small amount of ether. The mixture was then cooled in a freezer for 20 min. The resulting solid was suction filtered, washed with hexane and dried to give 2.17 g (83% yield) of the product as a tan solid, M.P. 56-60°; GC/MS: m/z 209. 1H NMR (CDCl3): δ 7.86 (s, 1H), 7.16 (m, 1H), 6.63 (m, 1H), 3.12 (s, 3H), 3.10 (s, 3H).

Workup

  1. temperatureto reflux for 1 h
  2. customThe solvent was removed in vacuo
  3. temperatureThe mixture was then cooled in a freezer for 20 min
  4. filtrationfiltered
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-230581bf8a63471ca9c3efcd8aacc418
Source dataset
uspto-grants-2015_04
Patent number
US09000162B2

Reaction notes

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