Triethylamine → (2E)-3-(5-Chloro-1-benzothien-2-yl)acryloylazide

HRID 1896495Notes

Reaction equation

HRID 1896495 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](/[CH:10]=[CH:11]/[C:12](O)=[O:13])=[CH:7][C:6]=2[CH:15]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](/[CH:10]=[CH:11]/[C:12]([N:31]=[N+:32]=[N-:33])=[O:13])=[CH:7][C:6]=2[CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 62365Isobutyl chloroformateHCID 59198425HCID 59198425, compound

Product 1

HCID 86639253(2E)-3-(5-Chloro-1-benzothien-2-yl)acryloylazide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of (2E)-3-(5-chloro-1-benzothien-2-yl)acrylic acid in acetone (0.2 M) at 0° C. were added Et3N (1.3 equiv) followed by isobutyl chloroformate (1.3 equiv). After stirring for 1 h, H2O solution (2 M) of NaN3 (1.3 equiv) was then added. The resulting mixture was stirred for a period of 0.5 h at 0° C. and 30 min at room temperature. H2O was then added followed by filtration and wash with H2O to provide the title compound.

Workup

  1. stirringThe resulting mixture was stirred for a period of 0.5 h at 0° C. and 30 min at room temperature
  2. filtrationfollowed by filtration
  3. washwash with H2O

Sources & evidence

ORD record
ord-c54d3f199b494dff80f6808ec0fa9f6e
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

Loading…