1,2-Dichloroethane → Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate

HRID 1776491Notes

Reaction equation

HRID 1776491 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18](=[O:23])[CH2:19][C:20](O)=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:20](=[O:21])[CH2:19][C:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:23])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 660384-(Methylthio)anilineHCID 1816593-(Benzyloxy)-3-oxopropanoic acid

Product 1

HCID 86679443Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoateYield 45.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(methylthio)aniline (500 mg, 3.59 mmol), 3-(benzyloxy)-3-oxopropanoic acid (1046 mg, 5.39 mmol), DMAP (527 mg, 4.31 mmol), and EDC (1377 mg, 7.18 mmol) were dissolved in DMF (7 ml). The reaction was stirred at RT for 4 hours. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate (520 mg, 45.9% yield).

Workup

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0ea2da153e1248f7884524b53c5a4582
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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