Toluene → HCID 68845325, compound

HRID 1948593Notes

Reaction equation

HRID 1948593 reaction equation
[CH2:1]([O:3][C:4](=O)[CH2:5][CH2:6]Br)[CH3:2].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][C:15]#[N:16].[CH3:17][C:18]([OH:20])=O.[OH2:21].[C:22]1(C)C=CC=CC=1>>[C:15]([C:14]1([C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])[C:18](=[O:20])[CH2:17][CH2:22]1)#[N:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 68320Ethyl 3-bromopropionateHCID 728802-ThienylacetonitrileHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 68845325HCID 68845325, compound

Conditions

Temperature
-10 °C

Procedure

Ethyl-3-bromopropionate (33.8 g) was added to a solution of 2-(thiophen-2-yl)acetonitrile (10 g) in toluene (300 ml) and the mixture was cooled to −10° C. NaNH2 (27 g) was added in portions over a period of 1 hour (the temperature was maintained below 0° C.). The reaction mixture was heated to RT and refluxed for 1 hour (111° C.). Finally the mixture was cooled to 0°-5° C. and AcOH/water (50 ml/100 ml) was added. The toluene phase was separated and the aqueous phase was extracted with toluene (3×200 ml). The combined organic extracts were washed with 5% Na2CO3 solution (1×50 ml) and water (1×00 ml) and dried over Na2SO4. The solvent was removed under reduced pressure.

Workup

  1. temperaturewas maintained below 0° C.)
  2. temperatureThe reaction mixture was heated to RT
  3. temperaturerefluxed for 1 hour (111° C.)
  4. temperatureFinally the mixture was cooled to 0°-5° C.
  5. customThe toluene phase was separated
  6. extractionthe aqueous phase was extracted with toluene (3×200 ml)
  7. washThe combined organic extracts were washed with 5% Na2CO3 solution (1×50 ml) and water (1×00 ml)
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e6e8a002fef44f3faf3f24ab1af372de
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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