Hydrochloric Acid → Ethyl 1-[(E)-benzylideneamino]cyclopropane-1-carboxylate

HRID 1632926Notes

Reaction equation

HRID 1632926 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][N:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].Br[CH2:16][CH2:17]Br.Cl>C(OCC)C.CS(C)=O.O>[CH:7](=[N:6][C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 357745Ethyl 2-(benzylideneamino)acetate

Product 1

HCID 12783664Ethyl 1-[(E)-benzylideneamino]cyclopropane-1-carboxylateYield 68%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

260 g (2.3 moles) of potassium tert.-butylate are added a little at a time to 200 g (1.05 moles) of N-benzylideneglycine ethyl ester and 90.5 ml (1.05 moles) of 1,2-dibromoethane in 900 ml of dry diethyl ether and 300 l of dry dimethylsulfoxide, so that the well-stirred mixture remains at from 25° to 35° C. The mixture is stirred at room temperature overnight and excess base is then neutralized by addition of 4N hydrochloric acid. The mixture is diluted with 1.5 l of water and the ethereal phase is separated off, washed with twice 300 ml of water, dried with sodium sulfate and evaporated to give 155 g (68%) of ethyl N-benzylidene-1-aminocyclopropanecarboxylate as an oil.

Workup

  1. customremains at from 25° to 35° C
  2. customthe ethereal phase is separated off
  3. washwashed with twice 300 ml of water
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-cbda66656f304d7691e1c9f9d409849d
Source dataset
uspto-grants-1984_10
Patent number
US04478758

Reaction notes

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