Ethanolamine → Ethyl 3-[2-(2-hydroxyethylcarbamoyl)phenyl]-2-methylacrylate

HRID 733275Notes

Reaction equation

HRID 733275 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:17])=[CH:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:5])[CH3:2].C(N(CC)CC)C.F[B-](F)(F)F.C([C:32](=[N:38]OC(N(C)C)=[N+](C)C)[C:33](OCC)=[O:34])#N.C(CN)O>CN(C)C=O>[OH:34][CH2:33][CH2:32][NH:38][C:10]([C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[CH:7]=[C:6]([CH3:17])[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:12]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471Triethylamine2×HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690545382-(2-Ethoxycarbonylpropen-1-yl)benzoic acid

Product 1

HCID 69053233Ethyl 3-[2-(2-hydroxyethylcarbamoyl)phenyl]-2-methylacrylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Ethyl 3-[2-(2-hydroxyethylcarbamoyl)phenyl]-2-methylacrylate is prepared as described in Example 30, starting with 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimethylformamide, a solution of 0.69 cm3 (5.0 mmol) of triethylamine and 1.64 g (5.0 mmol) of O-[(cyano(ethoxycarbonyl)methylene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (“TOTU”) in 6 cm3 of dimethylformamide, and a second solution consisting of 306 mg (5.0 mmol) of ethanolamine and 0.69 cm3 (5.0 mmol) of triethylamine in 10 cm3 of dimethylformamide. 1.14 g of ethyl 3-[2-(2-hydroxyethylcarbamoyl)phenyl]-2-methacrylate are thus obtained in the form of a yellowish oil, which can be reacted in the following step without further purification.

Sources & evidence

ORD record
ord-73830c54e7174f9f828b59c162d98f7e
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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