Dimethylamine → 4-[2-(Dimethylamino)-2-oxoethyl]benzeneacetic acid
Reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[CH3:15][NH:16][CH3:17]>CN(C)C=O.C([O-])([O-])=O.[K+].[K+]>[CH3:15][N:16]([CH3:17])[C:12](=[O:14])[CH2:11][C:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N'-Carbonyldiimidazole (11.4 g) was added to a stirred solution of 1,4-phenylenediacetic acid (11.4 g) in dry dimethylformamide (300 ml) under an atmosphere of nitrogen. The mixture was stirred at 20° for 2 h as dimethylamine gas (about 10 g) was bubbled through. The reaction mixture was then stirred at 20° for 3 h and evaporated in vacuo to leave a brown oil which was diluted with saturated K2CO3 solution (50 ml). The resulting mixture was evaporated in vacuo to leave an off-white solid which was triturated with EA (2×200 ml). The organic phase was discarded and the aqueous phase was acidified (pH1) with 5M hydrochloric acid to precipitate an off-white solid which was triturated with absolute ethanol (25 ml) and filtered to give the title compound (1.1 g) as a fine white solid m.p. 163°-165° (softening at 160°).
Workup
- customwas bubbled through
- customevaporated in vacuo
- customto leave a brown oil which
- customThe resulting mixture was evaporated in vacuo
- customto leave an off-white solid which
- customwas triturated with EA (2×200 ml)
- customto precipitate an off-white solid which
- customwas triturated with absolute ethanol (25 ml)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-27ca6a46d4c9461ca6f31d13f0c46ac9
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855314
Reaction notes
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