Acetic Acid → HCID 13578539, compound

HRID 465054Notes

Reaction equation

HRID 465054 reaction equation
[K].[O-]CCCC.[Cl:7]/[C:8](=[CH:11]/[N:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:13])/[C:9]#[N:10].C(O)(=O)C>C1(C)C=CC=CC=1>[NH2:10][C:9]1[C:8]([Cl:7])=[CH:11][N:12]([CH3:13])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 13578538Glycine, N-(2-chloro-2-cyanoethenyl)-N-methyl-, ethyl ester, (E)-

Product 1

HCID 13578539HCID 13578539, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Potassium ter.butoxide (0.5 g, 0.0044 mol) is placed in anhydrous toluene (300 ml). At ambient temperature, a solution of (E)-2-chloro-3-[[[(ethoxy)carbonyl]methyl](methyl)amino]-2-propene nitrile (58.0 g, 0.286 mol) (mp. 57° C.) in anhydrous toluene (200 ml) is added dropwise to the resulting suspension and the mixture is stirred for a further 30 minutes. It is then poured into ice water (1 liter), neutralized with acetic acid and then exhaustively extracted with dichloromethane. The combined extracts were dried over sodium sulphate and concentrated in vacuo. The residue remaining is recrystallized from diisopropyl ether/petroleum ether (1:1 v/v) and gives colorless crystals (50.0 g), m.p. 48° C.

Workup

  1. extractionexhaustively extracted with dichloromethane
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue remaining is recrystallized from diisopropyl ether/petroleum ether (1:1 v/v)

Sources & evidence

ORD record
ord-c2a0ecfa9826418fa358701ac0fd0e6d
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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