Methanimidamide, N,N-diphenyl- → 2-(3-Chlorobenzoyl)-3-phenylaminoacrylonitrile

HRID 251353

Reaction equation

HRID 251353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([CH2:7][C:8]#[N:9])=[O:6].[C:13]1([N:19](C2C=CC=CC=2)[CH:20]=N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([C:7](=[CH:20][NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]#[N:9])=[O:6]

Participants

4

Reactant 2

HCID 78296Methanimidamide, N,N-diphenyl-HCID 1408553-(3-Chlorophenyl)-3-oxopropanenitrile

Product 1

HCID 670242262-(3-Chlorobenzoyl)-3-phenylaminoacrylonitrileYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-chlorobenzoylacetonitrile (476 mg, 2.66 mmol, 1.0 eq) and diphenylformamidine (522 mg, 2.66 mmol, 1.0 eq) in 25 mL of toluene was stirred at room temperature for 2h then heated to 100° C. overnight. The solution was cooled and diluted with hexanes. The resulting solid was filtered and dried to provide the desired product (566 mg, 75%). HPLC (4 minute 10-95 gradient) tR 2.97 min; MS m/z 283.2 [M+H]+; 1H NMR (CDCl3), δ 8.06 (d, J=13.2 Hz, 1 H), 7.85 (m, 2 H), 7.46 (m, 4 H), 7.27 (m, 4 H) ppm.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-9085cda014cd40d6929d990b403aa4b3
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Linked notes

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