Ethyl bromoacetate → HCID 178472619, compound

HRID 1295836Notes

Reaction equation

HRID 1295836 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[NH:15].CC(C)([O-])C.CC(C)([O-])C.CC(C)([O-])C.[Al+3].[Br:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C)C=O>[Br-:32].[CH2:37]([O:36][C:34]([CH2:33][N:12]1[CH:13]=[CH:14][N+:10]([C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[C:11]1[NH2:15])=[O:35])[CH3:38]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 68399Aluminum tert-butoxideHCID 178425452HCID 178425452, compound

Product 1

HCID 178472619HCID 178472619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(2,4,6-trimethyl-phenyl)-imidazolidin-2-ylideneamine (3.00 g, 0.0148 mol) and aluminum tri-tert-butoxide (1.0 g, 0.0041 mol) in dimethylformamide (15 mL) was added ethyl bromoacetate (1.65 mL, 2.48 g, 0.00148 mol). The reaction mixture was allowed to stir at room temperature for 1 h, after which LC-MS indicated a 4:1 ratio of desired product to starting material. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give a pale orange-yellow solid, which was then treated twice with toluene to azeotropically remove any water. The solid was triturated with toluene, collected by filtration, and placed under high vacuum for 6 h. 1H NMR (CDCl3, 300 MHz) δ 7.01 (s, 2H), 4.87 (s, 2H), 4.29 (q, J=7 Hz, 2H), 3.96-3.89 (m, 4H), 2.32 (s, 3H), 2.25 (s, 6H), 1.34 (t, J=7 Hz, 3H). LC/MS: tR=0.92 min., (MH+)=290.43.

Sources & evidence

ORD record
ord-e57e273e6af54e1990f4a51b22845687
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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