Triethylamine → HCID 57845129, compound

HRID 1505629Notes

Reaction equation

HRID 1505629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[S:5][CH:6]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([N:25]=[N+:26]=[N-:27])=[O:11])[S:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 5708462(2E)-3-(4-Bromo-2-thienyl)-2-propenoic acid

Product 1

HCID 57845129HCID 57845129, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of (E)-3-(4-bromo-thiophen-2-yl)-acrylic acid (3.0 g, 12.9 mmol) in anhydrous acetone (20 ml) was cooled in an ice-bath to 0° C. and treated with triethylamine (2.15 ml, 15.4 mmol) and ethyl chloroformate (1.24 ml, 15.4 mmol). The reaction was left to stir for 0.5 h before being treated with a solution of sodium azide (1.0 g, 15.4 mmol) in distilled water (4 ml). After stirring for 1 h at 0° C., the reaction was further diluted with distilled water (40 ml) and extracted with DCM (3×25 ml). The organic layer was dried (MgSO4) and filtered for direct use in the next reaction.

Workup

  1. waitThe reaction was left
  2. stirringAfter stirring for 1 h at 0° C.
  3. extractionextracted with DCM (3×25 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered for direct use in the next reaction

Sources & evidence

ORD record
ord-ae04124ae1034ff38a4fc07450036596
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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