Formamide → HCID 66968816, compound

HRID 1424712Notes

Reaction equation

HRID 1424712 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[C:13]([C:15]1[CH:24]=[CH:23][C:18]([C:19](=O)[CH2:20]Br)=[CH:17][CH:16]=1)#[N:14].[CH:25]([NH2:27])=O>CN(C=O)C>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH:20]=[C:19]([C:18]3[CH:23]=[CH:24][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)[N:27]=[CH:25]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 986544-(Bromoacetyl)benzonitrileHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 66968816HCID 66968816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

4-Trifluoromethoxyaniline (2.20 g, 12.4 mmol) was added dropwise to a solution of 4-cyanophenacyl bromide (1.50 g, 6.7 mmol) in DMF (5 mL). This solution was then added to hot (180° C.) formamide (20 mL) over 5 min, and the combined solution was allowed to stir at 180° C. for 2 h. The cooled solution was then poured onto ice (100 mL), and extracted with ether (2×75 mL). After drying and concentrating, the resulting semi-solid was crystallized from MeOH/H2O. A second recrystallization from MeOH/H2O removed traces of the formanilide impurity and furnished pure product (200 mg): mp 155° C. Anal. Calcd. for C17H10F3N3O: C, 62.01; H, 3.06; N, 12.76. Found: C, 61.53; H, 3.13; N, 12.55.

Workup

  1. additionThe cooled solution was then poured onto ice (100 mL)
  2. extractionextracted with ether (2×75 mL)
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe resulting semi-solid was crystallized from MeOH/H2O
  6. customA second recrystallization from MeOH/H2O removed traces of the formanilide impurity

Sources & evidence

ORD record
ord-f8779550b7044734834e26a4cec335dc
Source dataset
uspto-grants-2015_01
Patent number
US08927729B2

Reaction notes

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