Ethyl chloroformate → HCID 86695275, compound

HRID 709412Notes

Reaction equation

HRID 709412 reaction equation
ClC(OCC)=O.[CH2:7]([O:9][C:10]([C:12]1[S:13][C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=1)=[O:11])[CH3:8].[N-:20]=[N+:21]=[N-:22].[Na+]>CC(C)=O.O>[N:20]([C:17]([C:14]1[S:13][C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])=[N:16][CH:15]=1)=[O:19])=[N+:21]=[N-:22]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 667149791357247-55-22×

Product 1

HCID 86695275HCID 86695275, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl chloroformate (9.8 g, 83.6 mmol) was added to a solution of 2-(ethoxycarbonyl)thiazole-5-carboxylic acid (Intermediate X, 13 g, 64.67 mmol), TEA (9.79 g, 97.01 mmol) in acetone (130 mL) at −20° C., stirred for 1 h, then a solution of NaN3 (5.4 g, 83.6 mmol) in water (15 mL) was added and stirred at RT for 30 mins. After completion, the solvent was evaporated, the crude residue was diluted with water (150 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford Ethyl 5-(azidocarbonyl)thiazole-2-carboxylate (11 g crude) as brown liquid. The crude was carried to next step without further purification.

Workup

  1. stirringstirred at RT for 30 mins
  2. customAfter completion, the solvent was evaporated
  3. additionthe crude residue was diluted with water (150 mL)
  4. extractionextracted with EtOAc (2×150 mL)
  5. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a5a4cd7d3c9d4c828b014b773f3378a2
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

Loading…