Formamide → HCID 66968825, compound

HRID 1189497Notes

Reaction equation

HRID 1189497 reaction equation
[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17](=O)[CH2:18]Br)=[CH:15][CH:14]=1)#[N:12].[CH:23]([NH2:25])=O>CN(C=O)C>[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH:18]=[C:17]([C:16]3[CH:21]=[CH:22][C:13]([C:11]#[N:12])=[CH:14][CH:15]=3)[N:25]=[CH:23]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 713FormamideHCID 759084-PropylanilineHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 66968825HCID 66968825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

4-Propylaniline (2.70 g, 20 mmol) was added dropwise to a solution of 4-cyanophenacyl bromide (2.20 g, 10 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 dark oil was purified by chromatography (3:1:2 hexanes:EtOAc:CH2Cl2). The first product (510 mg) was identified as 4-(5-propyl-1H-indol-3-yl)-benzonitrile, mp 140° C. The second fraction (275 mg) was identified as the desired imidazole: mp 133° C.; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J=6 Hz, 2H), 7.90 (s, 1H), 7.70 (d, J=6 Hz, 2H), 7.68 (s, 1H), 7.38 (d, J=4 Hz, 2H), 7.31 (d, J=4 Hz, 2H), 2.69 (t, J=8.9 Hz, 2H), 1.68 (m, 2H), 0.98 (t, J=7.5 Hz, 3H); ESIMS m/z 288.1 (M+H).

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 dark oil was purified by chromatography (3:1:2 hexanes:EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-f8b7a2c6d96643259327fa344fbc6251
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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