Triethylamine → 4-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

HRID 1919297Notes

Reaction equation

HRID 1919297 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[N:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1)=[C:15]=[O:16]>ClCCCl>[CH3:5][C:2]1([CH3:6])[C:3](=[NH:4])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:26])([F:27])[F:28])[CH:18]=2)[C:15](=[O:16])[NH:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 880222-Amino-2-methylpropionitrileHCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

Product 1

HCID 221169484-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrileYield 47.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of compound 9 (641 mg, 7.62 mmol) and triethylamine (168 mg, 1.66 mmol) in 1,2 dichloroethane (8.4 mL) at 0° C. under argon was dropwise added a solution of the isocyanate 8a (1.54 g, 7.28 mmol) in 1,2 dichloroethane (3.5 mL). The solution was stirred at 0° C. for 35 min and the ice bath was then removed and stirred at room temperature for an additional 30 min. The solution was then evaporated to dryness and purified by flash chromatography using EtOAc/Hexane (6:4) as an eluant to give pure compound 10a (1.02 g, 47%). 1H NMR (300 MHz, Acetone-d6) δ: 1.54 (m, 6H), 7.45 (broad s, 1H), 8.12 (d, 1H, J=8.46 Hz), 8.29 (dd, 1H, J1=6.90 Hz, J2=1.61 Hz), 8.46 (s, 1H), 8.51 (s, 1H).

Workup

  1. customthe ice bath was then removed
  2. stirringstirred at room temperature for an additional 30 min
  3. customThe solution was then evaporated to dryness
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2ea9b9cc3a25451b94dd4117a7368cd1
Source dataset
uspto-grants-2012_05
Patent number
US08168627B2

Reaction notes

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