Cyanoacetic acid → HCID 70873979, compound

HRID 2277430Notes

Reaction equation

HRID 2277430 reaction equation
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].C(Cl)(=O)C(Cl)=O.[CH2:13]([O:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])[CH3:14]>ClCCl.CN(C=O)C.O.C(=O)(O)[O-].[Na+]>[CH2:13]([O:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]([C:4](=[O:5])[CH2:3][C:1]#[N:2])[CH2:24][CH2:25][O:26][CH2:27][CH3:28])[CH3:14]

Participants

7

Reactant 3

HCID 9740Cyanoacetic acidHCID 65578Oxalyl chlorideHCID 70873910HCID 70873910, compound

Product 1

HCID 70873979HCID 70873979, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 86585896Sodium bicarbonate waterSolvent

Procedure

To a stirred mixture of commercially available cyanoacetic acid (1.1 eq, 0.118 g, 1.39 mmole) in dichloromethane was added oxalylchloride (0.353 g, 2.78 mmole, 0.236 mL) and 2 drops N,N′-dimethylformamide). The reaction was stirred for 2 hours at RT until homogenous solution developed. 2-(2-Ethoxy-ethylamino)-benzoic acid ethyl ester (1 eq, 0.300 g, 1.26 mmole) was added and the resulting solution was allowed to stir at RT overnight. Reaction mixture was diluted with saturated sodium bicarbonate water (20 mL) and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively With water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 2-[(2-Cyano-acetyl)-(2-ethoxy-ethyl)-amino]-benzoic acid ethyl ester as clear liquid (0.292 g, 76%, LCMS calc M+H 305, obs M+H 305).

Workup

  1. stirringto stir at RT overnight
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (25 mL×3)
  4. washCombined organic phase was washed consecutively With water, brine
  5. dry with materialbefore drying over sodium sulfate
  6. customOrganic phase was evaporated
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-18119793db294844b17af95702bd14b8
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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