Reaction equation
C(O[C:4]1[C:5](=[O:19])[C:6](=[O:18])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[OH:17])C.[CH3:20][C:21]([CH3:26])([CH3:25])[C@H:22]([NH2:24])[CH3:23].C(OCC)(=O)C>CCCCCC>[CH3:20][C:21]([CH3:26])([CH3:25])[C@H:22]([NH:24][C:4]1[C:5](=[O:19])[C:6](=[O:18])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[OH:17])[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-ethoxy-4-(2-hydroxy-4-cyanophenyl)amino-3-cyclobutene-1,2-dione (0.395 g, 0.0015 mol) and (R)-2,2,1-trimethylpropylamine (0.2M in ethanol, 23 ml, 0.0046 mol) was stirred at room temperature for two days. TLC (2:1 ethyl acetate:hexane) indicates a loss of starting material. The ethanol is evaporated on a rotary evaporator. The reaction is taken up in ethyl acetate and extracted well with 0.25N HCl. The organic layer is washed once with distilled water, dried (Na2SO4), and evaporated to a solid. The solid is collected and washed with diethyl ether to give 3-[(R)-2,2,1-trimethylpropylamino]-4-(2-hydroxy-4-cyanophenyl)amino-3-cyclobutene-1,2-dione, 0.345 g (0.00095 mol, 72%).
Workup
- customThe ethanol is evaporated on a rotary evaporator
- extractionextracted well with 0.25N HCl
- washThe organic layer is washed once with distilled water
- dry with materialdried (Na2SO4)
- customevaporated to a solid
- customThe solid is collected
- washwashed with diethyl ether
Sources & evidence
- ORD record
- ord-1382cf94d94b492d9eb0919e3544fdda
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840764
Linked notes
Loading…