Propylamine → Ethyl 2-methyl-3-(2-propylcarbamoylphenyl)acrylate

HRID 733270Notes

Reaction equation

HRID 733270 reaction equation
C(N(CC)CC)C.F[B-](F)(F)F.[C:13]([C:15](=NOC(N(C)C)=[N+](C)C)[C:16](OCC)=O)#[N:14].[CH2:30]([O:32][C:33]([C:35]([CH3:46])=[CH:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39]([OH:41])=O)=[O:34])[CH3:31].C(N)CC>CN(C)C=O>[CH3:46][C:35](=[CH:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39](=[O:41])[NH:14][CH2:13][CH2:15][CH3:16])[C:33]([O:32][CH2:30][CH3:31])=[O:34]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471Triethylamine2×HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690545382-(2-Ethoxycarbonylpropen-1-yl)benzoic acid

Product 1

HCID 69055286Ethyl 2-methyl-3-(2-propylcarbamoylphenyl)acrylateYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

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 is added at 0° C. to a solution of 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimethylformamide. After stirring for 30 minutes at 0° C. and then for 30 minutes at a temperature in the region of 20° C., this solution is introduced dropwise into a second solution consisting of 296 mg (5.0 mmol) of n-propylamine and 0.69 cm3 (5.0 mmol) of triethylamine in 10 cm3 of dimethylformamide, and the mixture is stirred for a further 6 hours at a temperature in the region of 20° C. After leaving the solution to stand overnight, the solvent is removed under vacuum and the residue is dissolved in ethyl acetate. After washing twice with sodium bicarbonate solution and then once with sodium chloride solution, the organic phase is dried over sodium sulfate and then concentrated. 1.10 g of ethyl 2-methyl-3-(2-propylcarbamoylphenyl)acrylate are thus obtained in the form of a yellowish oil, which can be reacted in the following step without further purification.

Workup

  1. waitfor 30 minutes at a temperature in the region of 20° C.
  2. additionthis solution is introduced dropwise into a second solution
  3. stirringthe mixture is stirred for a further 6 hours at a temperature in the region of 20° C
  4. customAfter leaving the solution
  5. waitto stand overnight
  6. customthe solvent is removed under vacuum
  7. dissolutionthe residue is dissolved in ethyl acetate
  8. washAfter washing twice with sodium bicarbonate solution
  9. dry with materialonce with sodium chloride solution, the organic phase is dried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f157b5e7d84209a0f4794829153fce
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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