Triethylamine → HCID 18005154, compound

HRID 481948Notes

Reaction equation

HRID 481948 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CC(C)=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([N:30]=[N+:31]=[N-:32])=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 62365Isobutyl chloroformateHCID 7364825-(Pyridin-2-yl)thiophene-2-carboxylic acid

Product 1

HCID 18005154HCID 18005154, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

20 g (97.45 mmol) of 5-(2-pyridyl)-thiophene-2-carboxylic acid are dissolved in 200 ml of acetone, and the solution is treated with 15.94 ml (115 mmol) of Et3N and cooled to 0° C. A solution of 14.85 ml (115 mmol) of isobutyl chloroformate in 88 ml of acetone is slowly added dropwise with stirring to the reaction solution thus obtained. After 1 h at 0° C., a solution of 9.5 g (146 mmol) of sodium azide in 44 ml of water is added dropwise, and the mixture is stirred at 0° C. for 1 h and allowed to come to room temperature. The reaction mixture is tipped onto ice water and the precipitate is filtered off with suction and reacted further as it is.

Workup

  1. customthus obtained
  2. stirringthe mixture is stirred at 0° C. for 1 h
  3. customto come to room temperature
  4. filtrationthe precipitate is filtered off with suction
  5. customreacted further as it

Sources & evidence

ORD record
ord-eaf6c676c0424e44ad78d1241b5fe490
Source dataset
uspto-grants-1998_08
Patent number
US05792765

Reaction notes

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